Literature DB >> 2125247

Preparations of 5-alkylmethylidene-3-carboxymethylrhodanine derivatives and their aldose reductase inhibitory activity.

Y Ohishi1, T Mukai, M Nagahara, M Yajima, N Kajikawa, K Miyahara, T Takano.   

Abstract

Reactions of 3-carboxymethylrhodanine (1) with aldehydes (2a-u) afforded stereoselectively the 5-mono-alkylmethylidene-3-carboxymethylrhodanines (3a-u). The configuration of the 5-monoalkylmethylidene-3-carboxymethylrhodanine (3k) were examined by X-ray structure analysis and confirmed to be Z-configuration. The stereoselective reaction path was discussed. Several 5-dialkylmethylidene-3-carboxymethylrhodanines (15a-f) and alkylamino derivatives of 3-carboxymethylrhodanines (18a-o) were also prepared. These products were evaluated for aldose reductase-inhibitory potency and half of them exhibited valuable inhibitory potency.

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Year:  1990        PMID： 2125247     DOI： 10.1248/cpb.38.1911

Source DB:  PubMed          Journal:  Chem Pharm Bull (Tokyo)        ISSN： 0009-2363            Impact factor:   1.645


  9 in total

1.  Three-component, one-flask synthesis of rhodanines (thiazolidinones).

Authors:  Alexander M Jacobine; Gary H Posner
Journal:  J Org Chem       Date:  2011-08-31       Impact factor: 4.354

2.  First small molecular inhibitors of T. brucei dolicholphosphate mannose synthase (DPMS), a validated drug target in African sleeping sickness.

Authors:  Terry K Smith; Benjamin L Young; Helen Denton; David L Hughes; Gerd K Wagner
Journal:  Bioorg Med Chem Lett       Date:  2009-01-30       Impact factor: 2.823

3.  Thiazolidinone CFTR inhibitors with improved water solubility identified by structure-activity analysis.

Authors:  N D Sonawane; A S Verkman
Journal:  Bioorg Med Chem       Date:  2008-07-23       Impact factor: 3.641

4.  Structure-based virtual screening, synthesis and SAR of novel inhibitors of hepatitis C virus NS5B polymerase.

Authors:  Tanaji T Talele; Payal Arora; Shridhar S Kulkarni; Maulik R Patel; Satyakam Singh; Maksim Chudayeu; Neerja Kaushik-Basu
Journal:  Bioorg Med Chem       Date:  2010-05-15       Impact factor: 3.641

5.  Synthesis and characterization of (Z)-5-arylmethylidene-rhodanines with photosynthesis-inhibiting properties.

Authors:  Veronika Opletalova; Jan Dolezel; Katarina Kralova; Matus Pesko; Jiri Kunes; Josef Jampilek
Journal:  Molecules       Date:  2011-06-22       Impact factor: 4.411

Review 6.  5-Ene-4-thiazolidinones - An efficient tool in medicinal chemistry.

Authors:  Danylo Kaminskyy; Anna Kryshchyshyn; Roman Lesyk
Journal:  Eur J Med Chem       Date:  2017-09-20       Impact factor: 6.514

7.  Design and synthesis of L- and D-phenylalanine derived rhodanines with novel C5-arylidenes as inhibitors of HCV NS5B polymerase.

Authors:  Bhargav A Patel; Ramalingam Krishnan; Nikhil Khadtare; K R Gurukumar; Amartya Basu; Payal Arora; Aaditya Bhatt; Maulik R Patel; Dibyendu Dana; Sanjai Kumar; Neerja Kaushik-Basu; Tanaji T Talele
Journal:  Bioorg Med Chem       Date:  2013-03-31       Impact factor: 3.641

8.  Photoisomerization of dicyanorhodanine-functionalized thiophenes.

Authors:  Cory T Kornman; Lei Li; Asmerom O Weldeab; Ion Ghiviriga; Khalil A Abboud; Ronald K Castellano
Journal:  Chem Sci       Date:  2020-09-09       Impact factor: 9.825

9.  Rhodanineacetic acid derivatives as potential drugs: preparation, hydrophobic properties and antifungal activity of (5-arylalkylidene-4-oxo-2-thioxo-1,3-thiazolidin-3-yl)acetic acids.

Authors:  Jan Dolezel; Petra Hirsova; Veronika Opletalova; Jiri Dohnal; Vejsova Marcela; Jiri Kunes; Josef Jampilek
Journal:  Molecules       Date:  2009-10-20       Impact factor: 4.411
  9 in total

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