ChemInform Abstract: SYNTHESIS AND PROPERTIES OF SOME NEW 4‐METHYL‐5‐THIAZOLECARBOXYLIC AND 4‐METHYL‐5‐THIAZOLEACETIC ACID DERIVATIVES

Abdel‐Lateef, M. F.‐A.; Rusek, D.; Cybulski, Jacek; Mizerski, A.; Eckstein, Z.

doi:10.1002/chin.197626207

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“…(1 R ,2 R )-2-Bromo- N -[2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1 H -1,2,4-triazol-1-yl)pr opyl]-4-methylthiazole-5-carboxamide (73). Method B ( 11 + 2-bromo-4-methylthiazole-5-carboxylic acid): white solid; mp 155−163 °C; 1 H NMR (300 MHz, CDCl 3 ) 7.81 (s, 1H), 7.78 (s, 1H), 7.35 (dt, J d = 6.5, J t = 8.8, 1H), 6.8−6.6 (m, 2H), 6.36 (br d, J = 9.5, 1H), 5.4 (br s, 1H), 5.00 (d, J = 14.2, 1H), 4.90 (br quint, J = 7, 1H), 4.46 (d, J = 14.2, 1H), 2.74 (s, 3H), 0.99 (d, J = 6.8, 3H); [α] D −97.8° ( c 1, CHCl 3 ). Anal.…”

Section: Methodsmentioning

confidence: 99%

New Azole Antifungals. 2. Synthesis and Antifungal Activity of Heterocyclecarboxamide Derivatives of 3-Amino-2-aryl-1-azolyl-2-butanol

et al. 1998

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A series of 92 azole antifungals containing an amido alcohol unit was synthesized. The nature and substitution of the amide portion was systematically modified in search of improved antifungal activity, especially against filamentous fungi. The compounds were tested in vitro against a variety of clinically important pathogens and in vivo (po) in a murine candidosis model. Thiazole and thiophene carboxamides carrying both a substituted phenyl ring and a small alkyl group were best suited for activity against filamentous fungi. In a subset of these compounds, the amide portion was conformationally locked by means of a pyrimidone ring and it was proven that only an orthogonal orientation of the phenyl ring yields bioactive products. A tendency to display long plasma elimination half-lives was observed in both series. Two compounds, 74 and 107, representative of the open and cyclic amides, respectively, were chosen for further studies, based on their excellent activity in in vivo murine models of candidosis and aspergillosis. This work describes the SARs found within this series. The next paper displays the results obtained in a related series of compounds, the quinazolinones.

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Section: Methodsmentioning

confidence: 99%

New Azole Antifungals. 2. Synthesis and Antifungal Activity of Heterocyclecarboxamide Derivatives of 3-Amino-2-aryl-1-azolyl-2-butanol

et al. 1998

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ChemInform Abstract: SYNTHESIS AND PROPERTIES OF SOME NEW 4‐METHYL‐5‐THIAZOLECARBOXYLIC AND 4‐METHYL‐5‐THIAZOLEACETIC ACID DERIVATIVES

Abstract: Durch Kondensation der entsprechenden Thioamide (I) mit den Chlorcarbonsäurederivaten (II) wurde eine Reihe von Thiazolcarbonsäurederivaten, wie z.B. (III) dargestellt, ferner durch alkalische Hydrolyse von (IIIc) die betreffenden Carbonsäuren, und in einigen Fällen die Anilide.

Cited by 1 publication

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New Azole Antifungals. 2. Synthesis and Antifungal Activity of Heterocyclecarboxamide Derivatives of 3-Amino-2-aryl-1-azolyl-2-butanol

New Azole Antifungals. 2. Synthesis and Antifungal Activity of Heterocyclecarboxamide Derivatives of 3-Amino-2-aryl-1-azolyl-2-butanol

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