NDLI: Synthesis, Reactions, and Pharmacological Screening of Heterocyclic Derivatives Using Nicotinic Acid as a Natural Synthon

Content Provider	Springer Nature Link
Author	Abd El Latif, Nehad A. Amr, Abd El Galil E. Ibrahiem, Alhusain A.
Copyright Year	2007
Abstract	A series of substituted pyridine derivatives were prepared from 3-acetylpyridine, which was prepared from the corresponding nicotinic acid as a natural starting material. Reaction of 3-acetylpyridine with indole-3-carboxaldehyde afforded the corresponding 3-β-(3-indolyl)acryloylpyridine, which was reacted with hydroxylamine hydrochloride in pyridine or acetic acid in the presence of sodium acetate to afford 3-β-(3-indolyl)acryloylpyridine oxime and oxazole derivatives. The oxime was treated with ethyl isothiocyanate or toluene-3,5-diisocyanate in refluxing dioxane to give the corresponding ethyl thiosemicarbazide and 3,5-bissemicarbazide derivative. 3-β-(3-Indolyl)acryloylpyridine was condensed with malononitrile in refluxing ethanol in the presence of piperidine as a catalyst to give cyanoaminopyrane, while it was condensed with ethyl cyanoacetate or malononitrile in the presence of ammonium acetate to yield cyanopyridone and cyanoaminopyridine derivatives. Cyclization of acryloylpyridine with o-phenylenediamine in refluxing butanol led to the formation of the corresponding benzodiazipine via the intermediate A. Finally, cycloaddition reaction of acryloylpyridine with thiourea yielded thioxopyrimidine, which was treated with chloroacetic acid to yield thiazolopyrimidine. An arylmethylene derivative was prepared by reacting thiazolopyrimidine with indole-3-carboxaldehyde or by reacting thioxopyrimidine with indole-3-carboxaldehyde and chloroacetic acid in one step. The pharmacological screening showed that many of these obtained compounds have good analgesic and anticonvulsant activities comparable to Valdecoxib® and Carbamazepine® as reference drugs.
Starting Page	559
Ending Page	567
Page Count	9
File Format	PDF
ISSN	00269247
Journal	Monatshefte für Chemie - Chemical Monthly
Volume Number	138
Issue Number	6
e-ISSN	14344475
Language	English
Publisher	Springer-Verlag
Publisher Date	2007-04-12
Publisher Place	Vienna
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	Chemistry/Food Science Analytical Chemistry Inorganic Chemistry Organic Chemistry Physical Chemistry Theoretical and Computational Chemistry
Content Type	Text
Resource Type	Article
Subject	Chemistry

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