Download PDF
Arzneimittelforschung 2003; 53(12): 857-863
DOI: 10.1055/s-0031-1299841
Antibiotics · Antiviral Drugs · Chemotherapeutics · Cytostatics
Editio Cantor Verlag Aulendorf (Germany)

Synthesis and Antifilarial Evaluation of 7-O-Acetamidyl-4-alkyl-2H-1-benzopyran-2-ones

Diksha Katiyar
a   Medicinal Chemistry, Central Drug Research Institute, Lucknow, India
,
Vinod Kumar Tiwari
a   Medicinal Chemistry, Central Drug Research Institute, Lucknow, India
,
Rama Pati Tripathi
a   Medicinal Chemistry, Central Drug Research Institute, Lucknow, India
,
Velurijagan Mohan Reddy
b   Biochemistry Central Drug Research Institute, Lucknow, India
,
Shailza Mishra Bhattacharya
c   Parasitology Divisions, Central Drug Research Institute, Lucknow, India
,
Jitendra Kumar Saxena
b   Biochemistry Central Drug Research Institute, Lucknow, India
› Author Affiliations
Further Information

Publication History

Publication Date:
25 December 2011 (online)

  PDF Download  Permissions and Reprints

Summary

A series of 7-O-acetamidyl-4-alkyl-2H-1-benzopyran-2-ones (5-23) has been synthesized by amidation of 7-O-(carbethoxymethyl)-4-alkyl-2H-1-benzopyran-2-ones (2a, 2b) with different primary and secondary amines in fair to good yield. The resulting compounds were screened for their filarial DNA topoisomerase inhibitory activity under in vivo condition in Setaria cervi. The compounds were tested in vitro against Brugia malayi. A few of the compounds possess promising antifilarial activity.

Zusammenfassung

Synthese und filarienhemmende Wirkung von 7-O-Acetamidyl-4-alkyl-2H-1-benzopyran-2-onen

Eine Reihe von 7-O-Acetamidyl-4-alkyl-2H-1-benzopyran-2-onen (5-23) wurde durch Amidierung von 7-O-(Carbethoxymethyl)-4-alkyl-2H-1-benzopyran2-onen (2a, 2b) mit unterschiedlichen Primärund Sekundäraminen synthetisiert. Die Ausbeute war zufriedenstellend bis gut. Die Verbindungen wurden in vivo auf ihre hemmende Wirkung gegen Filarien-DNA-Topoisomerase an Steria cervi sowie in vitro gegen Brugia malayi untersucht. Einige der Verbindugen besitzen eine vielversprechende filarienhemmende Wirkung.

Key words

7-O-Acetamidyl-4-alkyl-2H-1-benzopyran-2-ones, antifilarial activity - in vitro and in vivo studies - Antifilarial agents - Brugia malayi - Coumarins - DNA topoisomerase-II - Steria cervi