ChemInform Abstract: Synthesis, Antibacterial and Antimycobacterial Activities of Some New 4‐Aryl/Heteroaryl‐2,6‐dimethyl‐3,5‐bis‐N‐ (aryl)‐carbamoyl‐1,4‐dihydropyridines.

Sirisha, Kalam; Bikshapathi, Darna; Garlapati, Achaiah; Reddy, V. M.

doi:10.1002/chin.201131141

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“…Isoniazid having 4‐pyridine system in its structure is one of the frontline antituberculous drugs. Activity of pyridine derivatives against other bacterial species has been also reported .…”

Section: Introductionmentioning

confidence: 99%

The Synthesis and Antibacterial Activity of Novel 4-Pyrrolidin-3-cyanopyridine Derivatives

Bogdanowicz

Foks

Gobis

et al. 2013

J. Heterocyclic Chem.

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in Wiley Online Library (wileyonlinelibrary.com).2-Bromo-4-(pyrrolidin-1-yl)pyridine-3-carbonitrile obtained from 2-(1,3-bis(pyrrolidin-1-yl)allylidene) malononitrile has been used as a substrate for the synthesis of new cyanopyridine derivatives: 2-methoxy, 2-phenoxy, 2-aminoethylthio, and 2-thioxo. 4-(Pyrrolidin-1-yl)-2-thioxo-1,2-dihydropyridine-3-carbonitrile 7 in reaction with suitable alkyl and aminoalkyl halides gave respective sulfides. All synthesized compounds were evaluated for their antimicrobial activity against 26 aerobic and anaerobic bacteria. Determined minimal inhibitory concentration values ranged from 6.2 to 100 mg/mL. Derivatives 1, 3, 4, 6, and 12 were the most active compounds.J. Heterocyclic Chem., 50, 544 (2013). RESULTS AND DISCUSSIONMittelbach [13] reported the cyclization of 1,1-dicyano-4-(N,N-dimethylamino)-2-methoxy-1,3-butadiene with ammonia to give 2-amino-3-cyano-4-methoxypyridine (Scheme 1). We attempted the analogous cyclization of 1,1-dicyano-4-(N, N-dimethylamino)-2-methoxy-1,3-butadiene with pyrrolidine.The pyrrolidine ring should end up in 2-position of the pyridine ring, keeping the methoxy group in 4-position. Surprisingly, instead of the expected product, we obtained butadiene 1, the structure of which was confirmed by 1 H NMR spectroscopy and X-ray crystallography.The skeleton of 1 consists of conjugated system of single and multiple bonds including two pyrrolidine N atoms, which participate in the conjugation through their

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Section: Introductionmentioning

confidence: 99%