Synthesis, characterization and biological evaluation of tryptamine based benzamide derivatives (original) (raw)
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Synthesis and biological activity studies of new hybrid molecules containing tryptamine moiety
Medicinal Chemistry Research
The synthesis of N′-(4-substitutedphenylsulfonyl)-2-{4-[2-(1H-indol-yl)ethyl]-3-(4-chlorobenzyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl}acetohydrazides (3a–c), 2-{4-[2-(1H-indol-3-yl)ethyl]-3-(4-chlorobenzyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl}-N′-aryl methylidene acetohydrazides (4a–f) and 4-[2-(1H-indol-3-yl)ethyl]-5-(4-substitutedbenzyl)-2-[(5-sulfanyl-1,3,4-oxadiazol-2-yl)methyl]-2,4-dihydro-3H-1,2,4-triazol-3-ones (5a, b) was performed starting from the corresponding acid hydrazides (2a, b) which was reported earlier. The treatment of 1,3,4-oxadiazole derivatives (5a, b) with hydrazine hydrate produced 4-amino-5-sulfanyl-4H-1,2,4-triazol-3-yl derivatives (6a, b). Then, compound 6b was converted to the corresponding Schiff base (7) by the treatment with anisaldehyde. The synthesis of 5-(4-chlorobenzyl)-4-[2-(1H-indol-3-yl)ethyl]-2-[(4-benzyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)methyl]-2,4-dihydro-3H-1,2,4-triazol-3-one (8) and 5-(4-methylbenzyl)-4-[2-(1H-indol-3-yl)ethyl]-2-[(4-benzyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)methyl]-2,4-dihydro-3H-1,2,4-triazol-3-one (10) was carried out by the reaction of acid hydrazides (2a, b) with aryl iso(thio)cyanates either via the formation of the intermediates (9a, b) (for 10) or direct cyclization (for 8). 1,3-Oxa(thia)zol-2(3H)-ylidene]acetohydrazide derivatives (11a, b) were obtained by the reaction of 9a, b with 4-chlorophenacyl bromide. All newly synthesized compounds were screened for their antimicrobial activities and some of which was found to be active against the test microorganisms.
Taylor and Francic, 2023
Sulfonamide-based carboxamide drugs have multiple active sites that confers them with a variety of chemical and pharmacological activities. The combination of structural functionalities has been established to be vital in the drug discovery process. The synthesis of novel, nontoxic, cheap and effective anti-parasitic analogues is a trending aspect of pharmaceutical and medicinal chemistry research. In this research, the synthesis, characterization, and density functional theory (DFT) investigation of the reactivity and anti-trypanosomal simulation of benzenesulphonamide-based carboxamide derivatives was carried out for 2-[N-(benzenesulfonyl)-1-phenylformamido]-N-(4-nitrophenyl)acetamide(BPNA), 2-[N-(benzenesulfonyl)-1-phenylformamido]-N-(4-nitrophenyl)-3-phenylpropanamide (BPNPP), 2-[N-(benzenesulfonyl)-1-phenylformamido]-3-(1H-indol-2-yl)-N-(4-nitrophenyl)propenamide (BPINP) and 2-[N-(benzenesulfonyl)-1-phenylformamido]-4-methyl-N-(4-nitrophenyl)pentanamide (BPMNP) following an environmentally friendly zinc chloride catalyst mediated synthesis. The lower value of the HOMO-LUMO energy gap (2.9756 eV) observed for BPMNP indicated its higher chemical and biological activity. The global electrophilicity index (x), which is related to chemical hardness and chemical potential in line with other global descriptors showed that the order of reactivity is BPMNP > BPINP > BPNPP > BPNA. The NBO analysis showed that r ! r à , r à !p à , p ! p à , and p à ! p à transitions were observed in all the compounds while r ! r à and p à ! p à showed the lowest and the highest stabilization energy, respectively. From the molecular docking analysis, BPMNP again, showed the most stable binding energy of À 9.6 kcal/mol and bond length of 1.99 Å, evidently performing better than the standard drug with binding energy and bond length of À7.6 kcal/mol and 2.89 Å, respectively. The binding energy obtained was observed to follow a decreasing order as thus; BPMNP > BPINP > BPNA > BPNPP which strongly indicates alkane-substituted benzenesulphonamide carboxamides especially BPINP and BPMNP possess potent curative properties against trypanosomiasis.
Antibacterial investigation of two Benzamide derived compounds against some pathogenic bacteria
Journal of Survey in Fisheries Sciences
Antimicrobial drugs have become limited useful against nowadays pathogens; this was because of highly uptake and consumption of previously drugs which leads to gain the resistance potential by Pathogenic microbes generally and bacterial pathogens specifically. So in order to stop the mortality outcomes of these pathogens, we conducted our study to design new hopeful Benzamide derived Antibacterial drugs. Antibacterial investigation of two Benzamide derived compounds against some pathogenic bacteria 6247 in our study we obtained two Benzamide-derived compounds and diluted them in Dimethylsulfoxide (DMSO) at the concentration of (5 and 10mg/ml) and we used Gentamicin(Genta) as positive control, and then we checked them through two standardized antibacterial (Well diffusion and MTT-Microdilution) methods in order to get the IZ and MIC values and evaluate their potential against four common standard bacterial strains which where two gram negative: P. mirabilis (ATCC 14153) and K. pneumonia (ATCC 13883) with two gram positive: E. faecalis (ATCC 29212) and S. pneumoniae (ATCC 6303).in outcomes, our finding showed that both Compound 1 and 2 had only effects on E.faecalis which was (7 and 14mm) of IZ, respectively by only diffusion method. And they didn't have effects on the rest of bacterial strains. Nevertheless our positive control (Genta) had variable inhibition and killing effect against all bacterial strains.
Synthesis of Novel Tryptamine Derivatives and Their Biological Activity as Antitumor Agents
Molecules
We synthesized five novel tryptamine derivatives characterized by the presence of an azelayl chain or of a 1,1,1-trichloroethyl group, in turn connected to another heterocyclic scaffold. The combination of tryptamin-, 1,1,1-trichloroethyl- and 2-aminopyrimidinyl- moieties produced compound 9 identified as the most active compound in hematological cancer cell lines (IC50 = 0.57–65.32 μM). Moreover, keeping constant the presence of the tryptaminic scaffold and binding it to the azelayl moiety, the compounds maintain biological activity. Compound 13 is still active against hematological cancer cell lines and shows a selective effect only on HT29 cells (IC50 = 0.006 µM) among solid tumor models. Compound 14 loses activity on all leukemic lines, while showing a high level of toxicity on all solid tumor lines tested (IC50 0.0015–0.469 µM).
International Journal of Scientific Research in Science and Technology, 2020
The new series of substituted N-(phenylcarbamothioyl)benzamide derivatives (2a-2f) was designed, development and synthesized by using conventional and microwave method. In present work 6 different N-(phenylcarbamothioyl)benzamide were synthesized. Substituted benzoyl chloride is converted into benzoyl isothiocyanate by esterification. Benzoyl isothiocyanate is converted into Substituted (phenylcarbamothioyl)benzamide by treating with different types of substituted aniline. Confirmation of the chemical structure of the synthesized was substantiated by TLC, IR, 1H NMR, MS spectroscopy.Novel synthesized compounds screened for their in vivo and in-vitro anti-inflammatory studies and compound 2f shows promising anti-inflammatory activity.
Journal of Medicinal Chemistry, 2012
In our efforts to identify novel chemical scaffolds for the development of new antiprotozoal drugs, a compound library was screened against Toxoplasma gondii tachyzoites with activity discovered for N-(4-ethylbenzoyl)-2-hydroxybenzamide 1a against T. gondii as described elsewhere. Synthesis of a compound set was guided by T. gondii SAR with 1r found to be superior for T. gondii , also active against Thai and Sierra Leone strains of Plasmodium falciparum , and with superior ADMET properties as described elsewhere. Herein, synthesis methods and details of the chemical analysis of the compounds in this series are described. Further, this series of N-benzoyl-2-hydroxybenzamides was repurposed for testing against four other protozoan parasites: Trypanosoma brucei rhodesiense , Trypanosoma cruzi , Leishmania donovani , and P. falciparum (K1 isolate). Structure-activity analyses led to the identification of compounds in this set with excellent antileishmanial activity (compound 1d). Overall, compound 1r was the best and had activity 21-fold superior to that of the standard antimalarial drug chloroquine against the K1 P. falciparum isolate.
Synthesis and Antibacterial Study of Aaptamine Derivatives
Asian Journal of Chemistry, 2014
Aaptamine is a bioactive marine alkaloid containing a unique of 1H-benzo[de][1,6]naphthyridine skeleton. Aaptamine was isolated from marine sponge, Aaptos aaptos and was proposed as starting material for semi-synthetic modifications. A series of aaptamine derivatives were synthesized which consisted of 1,4-dialkyl (2-7), 4-alkyl (8-10) and 9-O-butyryl-1,4-dialkyl (11-16) aaptamine derivatives. Each derivative was characterized by FT-IR, UV-visible, NMR and MS. The synthesized compounds were evaluated for their antibacterial activity against Escherichia coli, Pseudomonas aeruginosa, Klebsiella pneumonia, Bacillus cereus, Staphylococcus aureus and Micrococcus sp. bacterial strains using the disc-diffusion method. Some of the derivatives showed potent antibacterial activity against certain bacterial strains.
Bioorganic & Medicinal Chemistry, 2007
A new series of N-(2-hydroxy-4(or 5)-nitro/aminophenyl)benzamide and phenylacetamide derivatives (1a–1n, 2a–2n) were synthesized and evaluated for antibacterial and antifungal activities against Staphylococcus aureus, Bacillus subtilis, Klebsiella pneumoniae, Pseudomonas aeruginosa, Escherichia coli, Candida albicans, and their drug-resistant isolate. Microbiological results indicated that the compounds possessed a broad spectrum of activity against the tested microorganisms at MIC values between 500 and 1.95 μg/ml. Benzamide derivative 1d exhibited the greatest activity with MIC values of 1.95, 3.9, and 7.8 μg/ml against drug-resistant B. subtilis, B. subtilis, and S. aureus, respectively.A new series of N-(2-hydroxy-4(or 5)-nitro/aminophenyl)benzamide and phenylacetamide derivatives (1a–1n, 2a–2n) were synthesized and evaluated for antibacterial and antifungal activities against Staphylococcus aureus, Bacillus subtilis, Klebsiella pneumoniae, Pseudomonas aeruginosa, Escherichia coli, Candida albicans, and their drug-resistant isolates. Microbiological results indicated that the compounds possessed a broad spectrum of activity against the tested microorganisms at MIC values between 500 and 1.95 μg/ml. Benzamide derivative 1d exhibited the greatest activity with MIC values of 1.95, 3.9, and 7.8 μg/ml against drug-resistant B. subtilis, B. subtilis, and S. aureus, respectively.