Journal ArticleDOI
Synthesis, chromatographic resolution, and anti-human immunodeficiency virus activity of (±)-calanolide A and its enantiomers
Michael T. Flavin,John D. Rizzo,Albert Khilevich,Alla Kucherenko,Abram Kivovich Sheinkman,Vilayphone Vilaychack,Lin Lin,Wei Chen,Eugenia Mata Greenwood,Thitima Pengsuparp,John M. Pezzuto,Stephen H. Hughes,Thomas M. Flavin,Michael Cibulski,William A. Boulanger,Robert L. Shone,Ze-Qi Xu +16 more
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TLDR
The anti-HIV agent (+/-)-calanolide A (1) has been synthesized in a five-step approach starting with phloroglucinol, which includes Pechmann reaction, Friedel-Crafts acylation, chromenylation with 4,4-dimethoxy- 2-methylbutan-2-ol, cyclization, and Luche reduction.Abstract:
The anti-HIV agent (±)-calanolide A (1) has been synthesized in a five-step approach starting with phloroglucinol [→ 5 → 6 → 11 → 18 → (±)-1], which includes Pechmann reaction, Friedel−Crafts acylation, chromenylation with 4,4-dimethoxy-2-methylbutan-2-ol, cyclization, and Luche reduction. Cyclization of chromene 11 to chromanone 18 was achieved by employing either acetaldehyde diethyl acetal or paraldehyde in the presence of trifluoroacetic acid and pyridine or PPTS. Luche reduction of chromanone 18 at lower temperature preferably yielded (±)-1. Reduction of chromone 12, synthesized by Kostanecki−Robinson reaction from chromene 11, failed to afford (±)-1. The synthetic (±)-1 has been chromatographically resolved into its optically active forms, (+)- and (−)-1. The anti-HIV activities for synthetic (±)-1, as well as resultant (+)- and (−)-1, have been determined. Only (+)-1 accounted for anti-HIV activity, which was similar to the data reported for the natural product, and (−)-1 was inactive.read more
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Cu@KCC‐1‐NH‐CS2 as a new and highly efficient nanocatalyst for the synthesis of 2‐amino‐4H‐chromene derivatives
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Pyranocoumarin compounds as a novel pharmacophore with anti-tb activity
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Eco-Efficient Synthesis of New Pyrido [2, 3-c] Coumarin Scaffolds Under Sonochemical Method
Praveen Chidurala,Venkateshwarlu Jetti,Ramakanth Pagadala,Jyotsna S. Meshram,Sreekanth B. Jonnalagadda +4 more
TL;DR: In this article, a green and simple approach to assembling pyrido[2,3-c]coumarin derivatives via one-pot multi-component condensation of 4-hydroxy-2H-chromen-2-one, benzaldehyde, acetoacetanilide, and ammonium acetate in the absence of catalyst in ethanol under ultrasound irradiation was explored.
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α-Glucosidase inhibitory activity, molecular docking, QSAR and ADMET properties of novel 2-amino-phenyldiazenyl-4H-chromene derivatives
Onkara Perumal,Sagar Vijay Kumar Peddakotla,Lingala Suresh,G. V. P. Chandramouli,Y. Pydisetty +4 more
TL;DR: α-Glucosidase inhibitory activity, molecular docking, QSAR and ADMET properties of novel 2-amino-phenyldiazenyl-4H-chromene derivatives derivatives and their properties are studied.
Journal ArticleDOI
Synthesis, spectroscopic characterization and crystallographic behavior of a biologically relevant novel indole-fused heterocyclic compound — Experimental and theoretical (DFT) studies
Sakshi Sharma,Goutam Brahmachari,Bubun Banerjee,Khondekar Nurjamal,Abhishek Kumar,Ambrish Kumar Srivastava,Neeraj Misra,Sarvesh Kumar Pandey,Rajnikant,Vivek K. Gupta +9 more
TL;DR: In this paper, an indole derivative - Ethyl 2'-amino-3'-cyano-6'-methyl-5-nitro-2-oxospiro [indoline-3,4'-pyran]-5'-carboxylate was synthesized in 87% yield.
References
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