ChemInform Abstract: Heterocyclic Derivatives of Sugars: The Formation of 1-Glycosyl-3-methylpyrazol-5-ones from Hydrazones (original) (raw)
Vignan’s Foundation for Science, Technology and Research, (Deemed to be University), 2019
Heterocyclic compounds are highly important class of organic compounds due to large number of applications such as pharmaceutical, biological, agrochemical, industrial, biotechnology, and material chemistry. In fact, the major pharmaceuticals, biologically active and agrochemicals are heterocyclic compounds. Large and variety of heterocyclic compounds are reported in the literature so far. The importance due to the design and the synthesis of heterocyclic chemistry is increasing rapidly day by day in synthetic and medicinal organic chemistry. The heterocyclic chemistry is recognized as an important discipline of general significance that hit the major aspects of recent chemical science, medicine, and organic chemistry. In the heterocyclic chemistry various structural motifs of the molecules provided pharmacological and biological activities to compounds. The Oxadiazoles motif is one of such significant heterocyclic motif, which play an important role in bio-isosteric and metabolically stable molecules, a replacement for the associate organic molecular unit. Indeed, 1,2,4-oxadiazoles have received tidy attention in the pharmaceutical industry as heterocyclic drug moieties. They have been utilized within the style of diverse biologically active templates like muscarinic agonists, trypsin enzyme inhibitors, opposed inflammatory agents, aminoalkane H3 antagonists, anticancer agents, and MAO inhibitors. Moreover, the derivative of chromene moiety leads to a wide range of biological activities due to their interactive nature with various protein moieties. Benzopyran derivatives are also exhibit important biological activities such as anticancer, antioxidant and antimicrobial activity etc. Furan and its derivatives exhibit biological activity such as in the defense system. They find applications as oxidants, antioxidants, as brightening agents, for drugs and in other fields of medicinal and agrochemistry. Benzofuran derivatives are also present in many natural products exhibits properties like physiological, pharmacological and toxic etc. They also display many applications like sedatives, anti-oxidants, pharmaceuticals, cosmetics etc. Moreover, benzofuran derivatives are also possess various pharmacological and biological activities such as antimicrobial, antibacterial, antifungal, antitubercular, antidiabetic, antidepressant, antioxidant, anticonvulsant and analgesic activities. In this context, in the first study, we focused on the design and synthesis of a series twelve 1,2,4-oxadiazole contained 8,9-dihydropyrano chromene moieties derivatives. All the twelve new derivatives were synthesized successfully and characterized by spectroscopic data and CHN analysis. Moreover, they were screened for antimicrobial study and they exhibited better microbial inhibition against selected microorganisms compared with the standard drug chloramphenicol. Among the many substitutes on the benzene ring, electronegative substituents such as chlorine, bromine etc. showed excellent biological activity. In the second part, we synthesized nine substituted-styryl furo-chromen-methanones, by reacting aryl-hydroxy-2H-chromenones with 2-bromo-1-(4-bromophenyl)ethanones under microwave strategy with high yields. All these newly synthesized compounds were characterized by spectral and CHN analysis. Additionally, they have been screened for antimicrobial study and these are exhibited better microbial inhibition against selected microorganisms. Among the many substitutes on the benzene ring, electronegative substituents like chlorine and bromine etc. showed excellent biological activity. Moreover, these biological evolution results were the good correlation with molecular docking studies too. In third part of work, we have developed a prototype facile and efficient, mild and straightforward method for the synthesis of 7’,9’-dihydrospiro [indoline-2,11’-pyrazolo [3,4-f] pyrimido [4,5-b] quinoline] -3,8’, 10’(1’H,6’H)-triones, by using acetic as a catalyst in ethanol solvent by this new MCR (a multicomponent reaction should be by definition performed one-pot) a three-component synthetic method, we achieved sixteen new trione derivatives with more operational simplicity, short reaction time and good yields (up to 93 %). We are confident that, this study provides a roadmap for the design and synthesis of new heterocyclic compounds for desired applications as drugs.
Arabian Journal of Chemistry, 2014
The multi-component reaction of 1-benzothiopyran-4-ones with heterocyclic amines and dimethylformamide-dimethylacetal (DMFDMA) in DMF at 150 °C under controlled microwave heating afforded novel poly-heterocyclic ring systems. Also, reaction of 3dimethylaminomethylene-1-benzothipyran-4-one with activemethylene derivatives was investigated. The structure of all products was established on the bases of spectral data and elemental analyses and alternative synthesis if possible. The prepared compounds were screened for their antitumor activity against HCT-116 "colon" cancer cell line and some derivatives showed promising activity. Abstract: The multi-component reaction of 1-benzothiopyran-4-ones with heterocyclic amines and dimethylformamide-dimethylacetal (DMFDMA) in DMF at 150 °C under controlled microwave heating afforded novel poly-heterocyclic ring systems. Also, reaction of 3dimethylaminomethylene-1-benzothipyran-4-one with activemethylene derivatives was investigated. The structure of all products was established on the bases of spectral data and elemental analyses and alternative synthesis if possible. The prepared compounds were screened for their antitumor activity against HCT-116 "colon" cancer cell line and some derivatives showed promising activity.
A REVIEW: BIOLOGICAL SIGNIFICANCES OF HETEROCYCLIC COMPOUNDS
Heterocyclic chemistry offers an example for the lack of distinct demarcations; in fact, it pervades the plurality of the other chemical disciplines. Heterocycles are inextricably woven into the life processes. The vital interest of the pharmaceutical and agrochemical industries in heterocycles is often connected with their natural occurrence. Synthetic chemistry provides cornucopia of heterocyclic systems. More than 90% of new drugs contain heterocycles and the interface between chemistry and biology, at which so much new scientific insight, discovery and application is taking place is crossed by heterocyclic compounds. This review article covers the most active heterocycles that have shown considerable biological actions as antifungal, anti-inflammatory, antibacterial, anticonvulsant, antiallergic, herbicidal, anticancer activity
Recent Developments on Synthetic Indoles as Potent Anticancer Agents
The indole ring system is the most privileged heterocycle in nature and embedded in many biological systems. The demonstration of many indole containing alkaloids as leads for the new pharmaceutical agents, the recognition of the importance of essential amino acid tryptophan in human nutrition and the discovery of plant hormones served to bring about a massive search on indole chemistry. This led to report vast number of structurally diversified bio-active natural and synthetic indoles. The present review focuses on the structure-based drug design of variety of classes of synthetic indoles as potent anticancer agents. Particularly, the recent developments on natural-product inspired rational synthesis of functionalized indoles, indolylazoles and bis(indoles) and their anticancer activities are presented. This review also drawn the attention towards combretastatin-based structural class of indoles and well discussed their potentials as tubulin polymerization inhibitors.
Developments in Quinoline Synthesis: A Review
Quinoline ring structure is obtained by o-condensation of benzene ring with pyridine. It is also called l-azanaphthalene or benzo[b]pyridine. Since first synthesis quinoline, number of methods has been discovered to enhance reaction yield, decrease reaction time as well as reduce hazardous reagents and reaction conditions. Compound with quinoline core are widely used for industrial purposes and also exhibit a broad range of biological activities. An overview of synthetic methodologies used for the construction of quinoline ring is also described.
Domino reactions in the synthesis of heterocyclic natural products and analogs
Domino reactions are defined as processes of two or more bond-forming reactions under identical conditions, in which the subsequent transformation takes place at the functionalities obtained in the former transformation. They allow the efficient synthesis of complex molecules from simple substrates in an ecologically and economically favorable way.
β-Oxodithioesters: a new frontier for diverse heterocyclic architectures
RSC Advances, 2013
Utilization of the fascinating properties of b-oxodithioesters as building blocks in heterocyclic frameworks was started a few decades ago. Its similarity and dissimilarity with b-ketoesters in terms of its synthesis or as a substrate towards synthesis makes it an interesting and emerging field of synthetic organic chemistry.