New Perspectives on the Chemotherapy of Malaria, Filariasis, and Leprosy

Elslager, Edward F.

doi:10.1007/978-3-0348-7087-0_10

Cited by 7 publications

(3 citation statements)

References 78 publications

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“…Fused pyrans 9a and b incorporated into spiro-thiazolidinedione and spiro-rhodanine frameworks were successfully installed in high yields and with good enantioselectivity ( ee up to >99%) and moderate diastereoselectivity (4:1 dr). It is noted that the fused thiopyranecycle and thiazolidine scaffolds are also reported to possess anticancer activity . The hetero-Diels–Alder cycloaddition of 6l to ethylvinylether (EVE) was carried out to create a new framework 10a in excellent yield (99%) and stereoselectivity.…”

Section: Resultsmentioning

confidence: 99%

Facile Construction of Structurally Diverse Thiazolidinedione-Derived Compounds via Divergent Stereoselective Cascade Organocatalysis and Their Biological Exploratory Studies

Zhang

Wang

et al. 2013

ACS Comb. Sci.

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In this article, we present a new approach by merging two powerful synthetic tactics, divergent synthesis and cascade organocatalysis, to create a divergent cascade organocatalysis strategy for the facile construction of new "privileged" substructure-based DOS (pDOS) library. As demonstrated, notably 5 distinct molecular architectures are produced facilely from readily available simple synthons thiazolidinedione and its analogues and α,β-unsaturated aldehydes in 1-3 steps with the powerful strategy. The beauty of the chemistry is highlighted by the efficient formation of structurally new and diverse products from structurally close reactants under the similar reaction conditions. Notably, structurally diverse spiro-thiazolidinediones and -rhodanines are produced from organocatalytic enantioselective 3-component Michael-Michael-aldol cascade reactions of respective thiazolidinediones and rhodanines with enals. Nevertheless, under the similar reaction conditions, reactions of isorhodanine via a Michael-cyclization cascade lead to structurally different fused thiopyranoid scaffolds. This strategy significantly minimizes time- and cost-consuming synthetic works. Furthermore, these molecules possess high structural complexity and functional, stereochemical, and skeletal diversity with similarity to natural scaffolds. In the preliminary biological studies of these molecules, compounds 4f, 8a, and 10a exhibit inhibitory activity against the human breast cancer cells, while compounds 8a, 9a, and 9b display good antifungal activities against Candida albicans and Cryptococcus neoformans. Notably, their structures are different from clinically used triazole antifungal drugs. Therefore, they could serve as good lead compounds for the development of new generation of antifungal agents.

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Section: Resultsmentioning

confidence: 99%

Facile Construction of Structurally Diverse Thiazolidinedione-Derived Compounds via Divergent Stereoselective Cascade Organocatalysis and Their Biological Exploratory Studies

Zhang

Wang

et al. 2013

ACS Comb. Sci.

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“…Compounds 2b,d,e, 3a,d,e,f, 9 and 10 were tested for their antimicrobial activity by the filter paper disc method [ 13 ] using the gram positive bacteria Staphlococcus aureus (NCTC-7447) and Bacillus cerus (ATCC-14579) and the gram negative bacteria Serratia marcesens (IMRU-70) and Proteus merabitis (NCTC-289). The results of antimicrobial activity tests are summarized in Table 1 .…”

Section: Biological Activitymentioning

confidence: 99%

Aminoacids in the Synthesis of Heterocyclic Systems: The Synthesis of Triazinoquinazolinones, Triazepinoquinazolinones and Triazocinoquinazolinones of Potential Biological Interest

et al. 2001

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“…Quinolines have oc cu pied a unique place in heterocyclic com pounds and have re mark ably con trib uted to bi olog i cal and me dic i nal chem is try. [1][2][3][4][5] Var i ous de riv a tives of pyrazole pos sess sig nif i cant an ti bac te rial, 6 antifungal 7 and anti-inflammatory 8 ac tiv i ties. The phar ma co log i cal prop erties of some pyrazoloquinolines as antiasthmatic, 9 anti tumor 10,11 and anti-inflammatory 12 agents have been re ported.…”

mentioning

confidence: 99%

Synthesis of New Pyrazolo[3,4‐b]quinolines, Thieno[2,3‐b]quinolines and Related Condensed Heterocyclic Systems

Bakhite

2001

J Chinese Chemical Soc

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3‐Amino‐1H‐pyrazolo[3,4‐b]quinoline (2) was reacted with benzaldehyde, acetylacetone, ethylacetoacetate and/or phenyl isothiocyanate to give compounds 3,4,5 and 6, respectively. The interaction of 6 with some α‐haloesters and/or α‐haloketones produced the corresponding thiazolidinones 7a‐c and thiazolines 9a‐d. 1H‐Pyrazolo[3,4‐b]quinoline‐3‐diazonium chloride (11) was coupled with some active methylene compounds to give the corresponding hydrazono compounds 12a,b and 13 which, in turn were cyclized into the corresponding triazinopyrazoloquinolines 14a,b and 15 by heating in acetic acid. 3‐Aminothieno[2,3‐b] quinoline‐2‐carbohydrazide (19) and 3‐amino‐2‐(1H‐benzimidazol‐2‐yl)thieno[2,3‐b]quinoline (21) were prepared and employed as key intermediates for synthesizing the second class of the title compounds.

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New Perspectives on the Chemotherapy of Malaria, Filariasis, and Leprosy

Cited by 7 publications

References 78 publications

Facile Construction of Structurally Diverse Thiazolidinedione-Derived Compounds via Divergent Stereoselective Cascade Organocatalysis and Their Biological Exploratory Studies

Facile Construction of Structurally Diverse Thiazolidinedione-Derived Compounds via Divergent Stereoselective Cascade Organocatalysis and Their Biological Exploratory Studies

Aminoacids in the Synthesis of Heterocyclic Systems: The Synthesis of Triazinoquinazolinones, Triazepinoquinazolinones and Triazocinoquinazolinones of Potential Biological Interest

Synthesis of New Pyrazolo[3,4‐b]quinolines, Thieno[2,3‐b]quinolines and Related Condensed Heterocyclic Systems

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