1995
DOI: 10.1002/jhet.5570320431
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A practical synthesis of 5‐(chloromethyl)furo[2,3‐b]pyridine, a key intermediate for the HIV protease inhibitor, L‐754,394

Abstract: A practical synthesis of 5‐(chloromethyl)furo[2,3‐b]pyridine (10), the side chain used to incorporate a key pharmacophore of the HIV protease inhibitor, L‐754,394, is described. The synthesis was accomplished in ten steps and in 15% overall yield from commercially available methyl 2‐furoate.

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Cited by 37 publications
(17 citation statements)
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“…Pyridone scaffold is present in a huge number of natural and synthetic biologically active compounds. 2‐Pyridone derivatives and their analogues have attracted considerable interest recently because of their anti‐microbial, anxiety, antitumor, antiviral, anticancer, antituberculosis, and anti‐inflammatory properties . Well‐known drugs amrinone (a) and milrinone (b) used for the treatment of heart failure contains 2‐pyridone moiety in their structure.…”
Section: Introductionmentioning
confidence: 99%
“…Pyridone scaffold is present in a huge number of natural and synthetic biologically active compounds. 2‐Pyridone derivatives and their analogues have attracted considerable interest recently because of their anti‐microbial, anxiety, antitumor, antiviral, anticancer, antituberculosis, and anti‐inflammatory properties . Well‐known drugs amrinone (a) and milrinone (b) used for the treatment of heart failure contains 2‐pyridone moiety in their structure.…”
Section: Introductionmentioning
confidence: 99%
“…Pyridine ring represents the main skeleton of numerous bioactive molecules. Recently 2-pyridone and their derivatives take interest due to their anti-inflammatory, antiviral and antiproliferative activities [1][2][3]. Amrinone (I) [4] and Milrinone (II) [5] have been considered as cardiotonic drugs for the treatment of heart failure.…”
Section: Introductionmentioning
confidence: 99%
“…Novobiocin and chlorobiocin have reported as antimicrobials containing a coumarin skeleton [13]. Pyridone and their derivatives play a vital role in some biological processes and have significant chemical and pharmacological importance [14,15,16]. 2-Pyridones motifs found to possess useful pharmacological activities, such as analgesic [17], antimalarial [18], anti-HIV [19], phytotoxic [20], and antitumoral [21] properties.…”
Section: Introductionmentioning
confidence: 99%