Suvi Rajamaki - Academia.edu (original) (raw)

Papers by Suvi Rajamaki

Research paper thumbnail of A telescopic one-pot synthesis of β-lactam rings using amines as a convenient source of imines

RSC Advances, 2016

A facile synthetic approach to substituted β-lactams was designed, using secondary benzylic amine... more A facile synthetic approach to substituted β-lactams was designed, using secondary benzylic amines and acid chlorides as starting materials. The reactions proceeded smoothly and all the products were obtained in good yields.

Research paper thumbnail of CCDC 1476892: Experimental Crystal Structure Determination

An entry from the Cambridge Structural Database, the world's repository for small molecule cr... more An entry from the Cambridge Structural Database, the world's repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

Research paper thumbnail of The effects of physical activity on the association between self-reported stress and episodic memory performance

Recurrent stress has been found to impair brain structures essential to memory. The cognitive res... more Recurrent stress has been found to impair brain structures essential to memory. The cognitive reserve model suggests that physical activity supplies protection against memory decline in neuropathologies. The purpose of the present study was to explore whether leisure physical activity modifies the predicted negative effect stress has on memory. A sub-sample derived from the Betula Study comprised 267 participants between 50 and 65 years. Memory was assessed by a SPT free recall and stress by a self-report. Low and High frequency exercisers were analyzed separately. After age, sex and education were controlled for in hierarchical regression, results showed that stress significantly improved memory performance in Low exercisers but no significant effect in High exercisers. Thus, frequency of physical activity did not explain variation in memory performance. However, higher age did not have a negative influence on memory performance for the High exercisers.

Research paper thumbnail of Synthesis of heterocycles for OLED applications

Organic light-emitting diodes (OLEDs) have in recent decades gained increasing importance in ligh... more Organic light-emitting diodes (OLEDs) have in recent decades gained increasing importance in lightning and in displays, spreading fast outside simple laboratory research. This thesis concentrates on the synthesis of substituted heterocycles and their use in OLED applications. The first chapter describes the basic principles behind OLEDs and their development and uses up to date. It also provides an overview of the classes of organic compounds – both polymers and small molecules – used in OLED applications, and describes the effects of heterocycles in organic molecules used in OLED applications. The second chapter describes the synthesis and optical characterisation of trisubstituted triazines, and the synthesis of gold nanoparticles functionalised with substituted triazines. Physical and optical characterisation of most interesting compounds is also included. The third chapter concentrates on new synthetic strategies for the synthesis of functionalised indoles. The optical propertie...

Research paper thumbnail of Vibrational and optical characterization of s-triazine derivatives

Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2017

The optical and electron properties of three different s-triazine derivatives are investigated to... more The optical and electron properties of three different s-triazine derivatives are investigated to ascertain the role of the donor acceptor character in amine-triazine systems depending on the bridging radical of the ammine group. The three derivatives were obtained starting from three different ammine compounds allowing to achieve a structure with a triazine core, surrounded by three ammine group and terminated with cyano or methyl or oxy-methyl functional group. Experimental optical data were interpreted in view of the electronic insights gathered by means of density functional theory simulations on base compounds. As compared to the reference electron donating triazine core, the resulting compounds show different donor acceptor character, from electron accepting to electron donating feature. Among the analyzed derivatives, the cyano terminated ammino-triazine compound shows the most promising optical features for photonics and lighting applications.

Research paper thumbnail of Palladium‐Catalysed Dehydrogenative Generation of Imines from Amines. A Nature‐Inspired Route to Indoles

Advanced Synthesis & Catalysis

H‐substituted imines are elusive compounds formed when aldehydes or ketones are mixed with ammoni... more H‐substituted imines are elusive compounds formed when aldehydes or ketones are mixed with ammonia. However, this class of molecules can be prepared through selective removal of a hydrogen molecule from a primary amine using a transition metal catalyst. This biomimetic transformation, previously employed for the N‐alkylation of anilines, is applied here to a domino preparation of differently substituted indoles from aliphatic primary amines and arylhydrazines. Several different linear and branched aliphatic primary amines are oxidized with reusable palladium on charcoal to the corresponding primary imines entrapped as arylhydrazones that can be isolated as such. Arylhydrazones can be further converted into N‐alkylindole derivatives via an acid‐mediated indolisation reaction. The one‐pot domino hydrogen transfer Fischer indole synthesis under heterogeneous catalysis is also possible, giving access to diverse substituted indoles, including NH indoles obtained after deprotection of the...

Research paper thumbnail of Palladium-Catalysed Dehydrogenative Generation of Imines from Amines. A Nature-Inspired Route to Indoles via Cross-Couplings of Amines with Arylhydrazines

Advanced Synthesis & Catalysis, 2013

ABSTRACT H‐substituted imines are elusive compounds formed when aldehydes or ketones are mixed wi... more ABSTRACT H‐substituted imines are elusive compounds formed when aldehydes or ketones are mixed with ammonia. However, this class of molecules can be prepared through selective removal of a hydrogen molecule from a primary amine using a transition metal catalyst. This biomimetic transformation, previously employed for the N‐alkylation of anilines, is applied here to a domino preparation of differently substituted indoles from aliphatic primary amines and arylhydrazines. Several different linear and branched aliphatic primary amines are oxidized with reusable palladium on charcoal to the corresponding primary imines entrapped as arylhydrazones that can be isolated as such. Arylhydrazones can be further converted into N‐alkylindole derivatives via an acid‐mediated indolisation reaction. The one‐pot domino hydrogen transfer Fischer indole synthesis under heterogeneous catalysis is also possible, giving access to diverse substituted indoles, including NH indoles obtained after deprotection of the corresponding benzyl compounds. The truly heterogeneous nature of the catalyst was demonstrated by recycling the catalyst in the same reaction, and in other palladium‐catalysed transformations.

Research paper thumbnail of BRIDGING SCIENCE AND BUSINESS: AN ETHNO-DRAMATIC APPROACH

The proceedings of SCOS 2009, ed. 27 th Standing Conference on Organizational Symbolism Conference Proceedings, Copenhagen, Denmark & Malmö, Sweden, 8-11 July 2009

This paper looks at the process of a multidisciplinary team creating a university spin-off in the... more This paper looks at the process of a multidisciplinary team creating a university spin-off in the field of combinatory chemistry. A successful creation of a new business based on basic science requires an ability to integrate two traditionally separate fields of expertise, namely chemistry and business.

Research paper thumbnail of Synthesis of New Linear Guanidines and Macrocyclic Amidinourea Derivatives Endowed with High Antifungal Activity against Candida spp. and Aspergillus spp. †

Journal of Medicinal Chemistry, 2009

New linear and cyclic guanidines were synthesized and tested in vitro for their antifungal activi... more New linear and cyclic guanidines were synthesized and tested in vitro for their antifungal activity toward clinically relevant strains of Candida species, in comparison to fluconazole. Macrocyclic compounds showed a minimum inhibitory concentration in the micromolar range and a biological activity profile in some cases better than that of fluconazole. One macrocyclic derivative was also tested against Aspergillus species and showed high antifungal activity comparable to that of amphotericin B and itraconazole.

Research paper thumbnail of A Mild and Efficient Synthesis of Substituted Quinolines via a Cross-Dehydrogenative Coupling of (Bio)available Alcohols and Aminoarenes

Advanced Synthesis & Catalysis, 2015

ABSTRACT A ruthenium-catalysed dehydrogenative cross-coupling of primary alcohols and imines in t... more ABSTRACT A ruthenium-catalysed dehydrogenative cross-coupling of primary alcohols and imines in the presence of TFA provided a library of differently substituted quinolines. Imines can be prepared in situ from various anilines and several benzyl alcohols using a ruthenium-catalysed hydrogen-transfer procedure. Without changing the catalyst, quinolines can be obtained in moderate to good yields by adding various primary alcohols in the presence of TFA (30 mol%) via a "telescopic" protocol. The use of alcohols, the absence of strong oxidants and the diversity of potential starting materials make this modern version of the Skraup reaction superior to most of the conventional quinoline syntheses.

Research paper thumbnail of Novel Substituted Aminoalkylguanidines as Potential Antihyperglycemic and Food Intake-Reducing Agents

Journal of Medicinal Chemistry, 2008

We report the synthesis and evaluation of aminoalkylguanidine analogues and derivatives in C57BL/... more We report the synthesis and evaluation of aminoalkylguanidine analogues and derivatives in C57BL/KsJ db/db diabetic mice, following identification by random screening of 1a and 1b as potential antihyperglycemics and/or modulators of food intake. These compounds are related to galegine, a gamma,gamma-dimethylallylguanidine. Between the newly identified compounds, 1h N-(cyclopropylmethyl)- N'-(4-(aminomethyl)cyclohexylmethyl)guanidine showed the most balanced activity as antihyperglycemic and food intake-reducing agent.

Research paper thumbnail of Lewis Acid Mediated endo-Cyclization of Trimethylsilylmethylenecyclopropyl Imines — A Stereoselective Route to Indolizidines

Cheminform, 2005

For Abstract see ChemInform Abstract in Full Text.

Research paper thumbnail of Novel Substituted Aminoalkylguanidines as Potential Antihyperglycemic and Food Intake-Reducing Agents

Journal of Medicinal Chemistry, 2008

We report the synthesis and evaluation of aminoalkylguanidine analogues and derivatives in C57BL/... more We report the synthesis and evaluation of aminoalkylguanidine analogues and derivatives in C57BL/KsJ db/db diabetic mice, following identification by random screening of 1a and 1b as potential antihyperglycemics and/or modulators of food intake. These compounds are related to galegine, a gamma,gamma-dimethylallylguanidine. Between the newly identified compounds, 1h N-(cyclopropylmethyl)- N'-(4-(aminomethyl)cyclohexylmethyl)guanidine showed the most balanced activity as antihyperglycemic and food intake-reducing agent.

Research paper thumbnail of Lewis acid mediated endo-cyclisation of trimethylsilylmethylenecyclopropyl imines?a stereoselective route to indolizidines

Chemical Communications, 2005

Lewis acid mediated endo-cyclisation of trimethylsilylmethylenecyclopropyl imines provides a ster... more Lewis acid mediated endo-cyclisation of trimethylsilylmethylenecyclopropyl imines provides a stereoselective route to indolizidines via a novel cascade sequence.

Research paper thumbnail of Synthesis of New Linear Guanidines and Macrocyclic Amidinourea Derivatives Endowed with High Antifungal Activity against Candida spp. and Aspergillus spp

Journal of Medicinal Chemistry, 2009

New linear and cyclic guanidines were synthesized and tested in vitro for their antifungal activi... more New linear and cyclic guanidines were synthesized and tested in vitro for their antifungal activity toward clinically relevant strains of Candida species, in comparison to fluconazole. Macrocyclic compounds showed a minimum inhibitory concentration in the micromolar range and a biological activity profile in some cases better than that of fluconazole. One macrocyclic derivative was also tested against Aspergillus species and showed high antifungal activity comparable to that of amphotericin B and itraconazole.

Research paper thumbnail of Toward novel HIV1 integrase binding inhibitors: Molecular modeling, synthesis, and biological studies

Bioorganic & Medicinal Chemistry Letters, 2007

The identification of a novel hit compound as integrase binding inhibitor has been accomplished b... more The identification of a novel hit compound as integrase binding inhibitor has been accomplished by means of virtual screening techniques. A small family of structurally related molecules has been synthesized and biologically evaluated with one of the compounds showing an IC50 = 12 μM.

Research paper thumbnail of Exploration of novel thiobarbituric acid-, rhodanine- and thiohydantoin-based HIV1 integrase inhibitors

Bioorganic & Medicinal Chemistry Letters, 2009

A novel compound inhibiting HIV-1 integrase has been identified by means of virtual screening tec... more A novel compound inhibiting HIV-1 integrase has been identified by means of virtual screening techniques. A small family of structurally related molecules has been synthesized and biologically evaluated with some of the compounds possessing micromolar activity both in enzymatic and cellular assays.A novel compound inhibiting HIV-1 integrase has been identified by means of virtual screening techniques. A small family of structurally related molecules has been synthesized and biologically evaluated with some of the compounds possessing micromolar activity both in enzymatic and cellular assays.

Research paper thumbnail of A telescopic one-pot synthesis of β-lactam rings using amines as a convenient source of imines

RSC Advances, 2016

A facile synthetic approach to substituted β-lactams was designed, using secondary benzylic amine... more A facile synthetic approach to substituted β-lactams was designed, using secondary benzylic amines and acid chlorides as starting materials. The reactions proceeded smoothly and all the products were obtained in good yields.

Research paper thumbnail of CCDC 1476892: Experimental Crystal Structure Determination

An entry from the Cambridge Structural Database, the world's repository for small molecule cr... more An entry from the Cambridge Structural Database, the world's repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

Research paper thumbnail of The effects of physical activity on the association between self-reported stress and episodic memory performance

Recurrent stress has been found to impair brain structures essential to memory. The cognitive res... more Recurrent stress has been found to impair brain structures essential to memory. The cognitive reserve model suggests that physical activity supplies protection against memory decline in neuropathologies. The purpose of the present study was to explore whether leisure physical activity modifies the predicted negative effect stress has on memory. A sub-sample derived from the Betula Study comprised 267 participants between 50 and 65 years. Memory was assessed by a SPT free recall and stress by a self-report. Low and High frequency exercisers were analyzed separately. After age, sex and education were controlled for in hierarchical regression, results showed that stress significantly improved memory performance in Low exercisers but no significant effect in High exercisers. Thus, frequency of physical activity did not explain variation in memory performance. However, higher age did not have a negative influence on memory performance for the High exercisers.

Research paper thumbnail of Synthesis of heterocycles for OLED applications

Organic light-emitting diodes (OLEDs) have in recent decades gained increasing importance in ligh... more Organic light-emitting diodes (OLEDs) have in recent decades gained increasing importance in lightning and in displays, spreading fast outside simple laboratory research. This thesis concentrates on the synthesis of substituted heterocycles and their use in OLED applications. The first chapter describes the basic principles behind OLEDs and their development and uses up to date. It also provides an overview of the classes of organic compounds – both polymers and small molecules – used in OLED applications, and describes the effects of heterocycles in organic molecules used in OLED applications. The second chapter describes the synthesis and optical characterisation of trisubstituted triazines, and the synthesis of gold nanoparticles functionalised with substituted triazines. Physical and optical characterisation of most interesting compounds is also included. The third chapter concentrates on new synthetic strategies for the synthesis of functionalised indoles. The optical propertie...

Research paper thumbnail of Vibrational and optical characterization of s-triazine derivatives

Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2017

The optical and electron properties of three different s-triazine derivatives are investigated to... more The optical and electron properties of three different s-triazine derivatives are investigated to ascertain the role of the donor acceptor character in amine-triazine systems depending on the bridging radical of the ammine group. The three derivatives were obtained starting from three different ammine compounds allowing to achieve a structure with a triazine core, surrounded by three ammine group and terminated with cyano or methyl or oxy-methyl functional group. Experimental optical data were interpreted in view of the electronic insights gathered by means of density functional theory simulations on base compounds. As compared to the reference electron donating triazine core, the resulting compounds show different donor acceptor character, from electron accepting to electron donating feature. Among the analyzed derivatives, the cyano terminated ammino-triazine compound shows the most promising optical features for photonics and lighting applications.

Research paper thumbnail of Palladium‐Catalysed Dehydrogenative Generation of Imines from Amines. A Nature‐Inspired Route to Indoles

Advanced Synthesis & Catalysis

H‐substituted imines are elusive compounds formed when aldehydes or ketones are mixed with ammoni... more H‐substituted imines are elusive compounds formed when aldehydes or ketones are mixed with ammonia. However, this class of molecules can be prepared through selective removal of a hydrogen molecule from a primary amine using a transition metal catalyst. This biomimetic transformation, previously employed for the N‐alkylation of anilines, is applied here to a domino preparation of differently substituted indoles from aliphatic primary amines and arylhydrazines. Several different linear and branched aliphatic primary amines are oxidized with reusable palladium on charcoal to the corresponding primary imines entrapped as arylhydrazones that can be isolated as such. Arylhydrazones can be further converted into N‐alkylindole derivatives via an acid‐mediated indolisation reaction. The one‐pot domino hydrogen transfer Fischer indole synthesis under heterogeneous catalysis is also possible, giving access to diverse substituted indoles, including NH indoles obtained after deprotection of the...

Research paper thumbnail of Palladium-Catalysed Dehydrogenative Generation of Imines from Amines. A Nature-Inspired Route to Indoles via Cross-Couplings of Amines with Arylhydrazines

Advanced Synthesis & Catalysis, 2013

ABSTRACT H‐substituted imines are elusive compounds formed when aldehydes or ketones are mixed wi... more ABSTRACT H‐substituted imines are elusive compounds formed when aldehydes or ketones are mixed with ammonia. However, this class of molecules can be prepared through selective removal of a hydrogen molecule from a primary amine using a transition metal catalyst. This biomimetic transformation, previously employed for the N‐alkylation of anilines, is applied here to a domino preparation of differently substituted indoles from aliphatic primary amines and arylhydrazines. Several different linear and branched aliphatic primary amines are oxidized with reusable palladium on charcoal to the corresponding primary imines entrapped as arylhydrazones that can be isolated as such. Arylhydrazones can be further converted into N‐alkylindole derivatives via an acid‐mediated indolisation reaction. The one‐pot domino hydrogen transfer Fischer indole synthesis under heterogeneous catalysis is also possible, giving access to diverse substituted indoles, including NH indoles obtained after deprotection of the corresponding benzyl compounds. The truly heterogeneous nature of the catalyst was demonstrated by recycling the catalyst in the same reaction, and in other palladium‐catalysed transformations.

Research paper thumbnail of BRIDGING SCIENCE AND BUSINESS: AN ETHNO-DRAMATIC APPROACH

The proceedings of SCOS 2009, ed. 27 th Standing Conference on Organizational Symbolism Conference Proceedings, Copenhagen, Denmark & Malmö, Sweden, 8-11 July 2009

This paper looks at the process of a multidisciplinary team creating a university spin-off in the... more This paper looks at the process of a multidisciplinary team creating a university spin-off in the field of combinatory chemistry. A successful creation of a new business based on basic science requires an ability to integrate two traditionally separate fields of expertise, namely chemistry and business.

Research paper thumbnail of Synthesis of New Linear Guanidines and Macrocyclic Amidinourea Derivatives Endowed with High Antifungal Activity against Candida spp. and Aspergillus spp. †

Journal of Medicinal Chemistry, 2009

New linear and cyclic guanidines were synthesized and tested in vitro for their antifungal activi... more New linear and cyclic guanidines were synthesized and tested in vitro for their antifungal activity toward clinically relevant strains of Candida species, in comparison to fluconazole. Macrocyclic compounds showed a minimum inhibitory concentration in the micromolar range and a biological activity profile in some cases better than that of fluconazole. One macrocyclic derivative was also tested against Aspergillus species and showed high antifungal activity comparable to that of amphotericin B and itraconazole.

Research paper thumbnail of A Mild and Efficient Synthesis of Substituted Quinolines via a Cross-Dehydrogenative Coupling of (Bio)available Alcohols and Aminoarenes

Advanced Synthesis & Catalysis, 2015

ABSTRACT A ruthenium-catalysed dehydrogenative cross-coupling of primary alcohols and imines in t... more ABSTRACT A ruthenium-catalysed dehydrogenative cross-coupling of primary alcohols and imines in the presence of TFA provided a library of differently substituted quinolines. Imines can be prepared in situ from various anilines and several benzyl alcohols using a ruthenium-catalysed hydrogen-transfer procedure. Without changing the catalyst, quinolines can be obtained in moderate to good yields by adding various primary alcohols in the presence of TFA (30 mol%) via a "telescopic" protocol. The use of alcohols, the absence of strong oxidants and the diversity of potential starting materials make this modern version of the Skraup reaction superior to most of the conventional quinoline syntheses.

Research paper thumbnail of Novel Substituted Aminoalkylguanidines as Potential Antihyperglycemic and Food Intake-Reducing Agents

Journal of Medicinal Chemistry, 2008

We report the synthesis and evaluation of aminoalkylguanidine analogues and derivatives in C57BL/... more We report the synthesis and evaluation of aminoalkylguanidine analogues and derivatives in C57BL/KsJ db/db diabetic mice, following identification by random screening of 1a and 1b as potential antihyperglycemics and/or modulators of food intake. These compounds are related to galegine, a gamma,gamma-dimethylallylguanidine. Between the newly identified compounds, 1h N-(cyclopropylmethyl)- N'-(4-(aminomethyl)cyclohexylmethyl)guanidine showed the most balanced activity as antihyperglycemic and food intake-reducing agent.

Research paper thumbnail of Lewis Acid Mediated endo-Cyclization of Trimethylsilylmethylenecyclopropyl Imines — A Stereoselective Route to Indolizidines

Cheminform, 2005

For Abstract see ChemInform Abstract in Full Text.

Research paper thumbnail of Novel Substituted Aminoalkylguanidines as Potential Antihyperglycemic and Food Intake-Reducing Agents

Journal of Medicinal Chemistry, 2008

We report the synthesis and evaluation of aminoalkylguanidine analogues and derivatives in C57BL/... more We report the synthesis and evaluation of aminoalkylguanidine analogues and derivatives in C57BL/KsJ db/db diabetic mice, following identification by random screening of 1a and 1b as potential antihyperglycemics and/or modulators of food intake. These compounds are related to galegine, a gamma,gamma-dimethylallylguanidine. Between the newly identified compounds, 1h N-(cyclopropylmethyl)- N'-(4-(aminomethyl)cyclohexylmethyl)guanidine showed the most balanced activity as antihyperglycemic and food intake-reducing agent.

Research paper thumbnail of Lewis acid mediated endo-cyclisation of trimethylsilylmethylenecyclopropyl imines?a stereoselective route to indolizidines

Chemical Communications, 2005

Lewis acid mediated endo-cyclisation of trimethylsilylmethylenecyclopropyl imines provides a ster... more Lewis acid mediated endo-cyclisation of trimethylsilylmethylenecyclopropyl imines provides a stereoselective route to indolizidines via a novel cascade sequence.

Research paper thumbnail of Synthesis of New Linear Guanidines and Macrocyclic Amidinourea Derivatives Endowed with High Antifungal Activity against Candida spp. and Aspergillus spp

Journal of Medicinal Chemistry, 2009

New linear and cyclic guanidines were synthesized and tested in vitro for their antifungal activi... more New linear and cyclic guanidines were synthesized and tested in vitro for their antifungal activity toward clinically relevant strains of Candida species, in comparison to fluconazole. Macrocyclic compounds showed a minimum inhibitory concentration in the micromolar range and a biological activity profile in some cases better than that of fluconazole. One macrocyclic derivative was also tested against Aspergillus species and showed high antifungal activity comparable to that of amphotericin B and itraconazole.

Research paper thumbnail of Toward novel HIV1 integrase binding inhibitors: Molecular modeling, synthesis, and biological studies

Bioorganic & Medicinal Chemistry Letters, 2007

The identification of a novel hit compound as integrase binding inhibitor has been accomplished b... more The identification of a novel hit compound as integrase binding inhibitor has been accomplished by means of virtual screening techniques. A small family of structurally related molecules has been synthesized and biologically evaluated with one of the compounds showing an IC50 = 12 μM.

Research paper thumbnail of Exploration of novel thiobarbituric acid-, rhodanine- and thiohydantoin-based HIV1 integrase inhibitors

Bioorganic & Medicinal Chemistry Letters, 2009

A novel compound inhibiting HIV-1 integrase has been identified by means of virtual screening tec... more A novel compound inhibiting HIV-1 integrase has been identified by means of virtual screening techniques. A small family of structurally related molecules has been synthesized and biologically evaluated with some of the compounds possessing micromolar activity both in enzymatic and cellular assays.A novel compound inhibiting HIV-1 integrase has been identified by means of virtual screening techniques. A small family of structurally related molecules has been synthesized and biologically evaluated with some of the compounds possessing micromolar activity both in enzymatic and cellular assays.