Literature DB >> 30310245

SYNTHESIS AND OPTICAL RESOLUTION OF HIGH AFFINITY P2-LIGANDS FOR HIV-1 PROTEASE INHIBITORS.

Arun K Ghosh1, Yan Chen1.   

Abstract

Racemic bis-tetrahydrofuran ligand 6 was efficiently synthesized utilizing catalytic cobaloxime 10 mediated radical cyclization as the key step. Optical resolution of the racemic alcohol with immobilized-Amano lipase, afforded optically pure ligands.

Entities:  

Year:  2000        PMID： 30310245      PMCID： PMC6177221          DOI： 10.1016/0040-4039(94)02296-N

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  2 in total

1.  Structure-based design of HIV-1 protease inhibitors: replacement of two amides and a 10 pi-aromatic system by a fused bis-tetrahydrofuran.

Authors:  A K Ghosh; W J Thompson; P M Fitzgerald; J C Culberson; M G Axel; S P McKee; J R Huff; P S Anderson
Journal:  J Med Chem       Date:  1994-08-05       Impact factor: 7.446

2.  Rational design of peptide-based HIV proteinase inhibitors.

Authors:  N A Roberts; J A Martin; D Kinchington; A V Broadhurst; J C Craig; I B Duncan; S A Galpin; B K Handa; J Kay; A Kröhn
Journal:  Science       Date:  1990-04-20       Impact factor: 47.728
  2 in total
  11 in total

1.  A Convenient Enzymatic Route to Optically Active l-Aminoindan-2-ol: Versatile Ligands for HIV-1 Protease Inhibitors and Asymmetric Syntheses.

Authors:  Arun K Ghosh; John F Kincaid; Michael G Haske
Journal:  Synthesis (Stuttg)       Date:  1997-05       Impact factor: 3.157

2.  cis-1-Aminoindan-2-ol in Asymmetric Syntheses.

Authors:  Arun K Ghosh; Steve Fidanze; Chris H Senanayake
Journal:  Synthesis (Stuttg)       Date:  1998-07       Impact factor: 3.157

3.  Design, Synthesis, and X-ray Studies of Potent HIV-1 Protease Inhibitors with P2-Carboxamide Functionalities.

Authors:  Arun K Ghosh; Alessandro Grillo; Jakka Raghavaiah; Satish Kovela; Megan E Johnson; Daniel W Kneller; Yuan-Fang Wang; Shin-Ichiro Hattori; Nobuyo Higashi-Kuwata; Irene T Weber; Hiroaki Mitsuya
Journal:  ACS Med Chem Lett       Date:  2020-03-03       Impact factor: 4.345

4.  A Stereoselective Anti-Aldol Route to (3R,3aS,6aR)-Hexahydrofuro[2,3-b] furan-3-ol: A Key Ligand for a New Generation of HIV Protease Inhibitors.

Authors:  Arun K Ghosh; Jianfeng Li; Ramu Sridhar Perali
Journal:  Synthesis (Stuttg)       Date:  2006-09       Impact factor: 3.157

5.  Synthesis of Bioactive Natural Products by Asymmetric syn- and anti-Aldol Reactions.

Authors:  Arun K Ghosh; Zachary L Dawson
Journal:  Synthesis (Stuttg)       Date:  2009-09       Impact factor: 3.157

6.  Nature Inspired Molecular Design: Stereoselective Synthesis of Bicyclic and Polycyclic Ethers for Potent HIV-1 Protease Inhibitors.

Authors:  Arun K Ghosh; Margherita Brindisi
Journal:  Asian J Org Chem       Date:  2018-06-08       Impact factor: 3.319

7.  Lewis Acid-Catalyzed Vinyl Acetal Rearrangement of 4,5-Dihydro-1,3-dioxepines: Stereoselective Synthesis of cis- and trans-2,3-Disubstituted Tetrahydrofurans.

Authors:  Arun K Ghosh; Miranda R Belcher
Journal:  J Org Chem       Date:  2020-08-05       Impact factor: 4.354

8.  Highly potent HIV-1 protease inhibitors with novel tricyclic P2 ligands: design, synthesis, and protein-ligand X-ray studies.

Authors:  Arun K Ghosh; Garth L Parham; Cuthbert D Martyr; Prasanth R Nyalapatla; Heather L Osswald; Johnson Agniswamy; Yuan-Fang Wang; Masayuki Amano; Irene T Weber; Hiroaki Mitsuya
Journal:  J Med Chem       Date:  2013-08-15       Impact factor: 7.446

9.  The Chiron Approach to (3R,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-ol, a Key Subunit of HIV-1 Protease Inhibitor Drug, Darunavir.

Authors:  Arun K Ghosh; Shivaji B Markad; William L Robinson
Journal:  J Org Chem       Date:  2020-12-03       Impact factor: 4.354

Review 10.  Organic carbamates in drug design and medicinal chemistry.

Authors:  Arun K Ghosh; Margherita Brindisi
Journal:  J Med Chem       Date:  2015-01-07       Impact factor: 7.446
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