Magnitudes of the inductive effects of the nitro and nitrate groups

Slovetskii, V. I.; Fainzil'berg, A. A.

doi:10.1007/bf01151397

Cited by 1 publication

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“…Differences in lipophilicity, basicity, − and magnitude of the dipole moment ,,− are observed (Figure ). Furazans are highly inductive, comparable to a trifluoromethyl or tetrazolyl group ,, (Figure ). The unique properties of furazans can impart interesting pharmacology to drug-like molecules.…”

Section: Physical Propertiesmentioning

confidence: 99%

“…A furazan bioisostere of indomethacin (25) enhanced selectivity for aldo-ketoreductase (AKR), an oncology drug target, over cyclooxygenase (COX) with minimal impact on the physical properties and antiproliferative effects (Table 2); a moderate increase in lipophilicity was observed. 42,43 Nonsteroidal anti-inflammatory drugs (NSAIDs) such as indomethacin are known to have anticancer activity, but their efficacy is limited by adverse gastrointestinal and cardiovascular responses related to effects on COX activity.…”

Section: ■ Introductionmentioning

confidence: 99%

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Furazans in Medicinal Chemistry

et al. 2021

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Incorporation of heterocycles into drug molecules can enhance physical properties and biological activity. A variety of heterocyclic groups is available to medicinal chemists, many of which have been reviewed in detail elsewhere. Oxadiazoles are a class of heterocycle containing one oxygen and two nitrogen atoms, available in three isomeric forms. While the 1,2,4- and 1,3,4-oxadiazoles have seen widespread application in medicinal chemistry, 1,2,5-oxadiazoles (furazans) are less common. This Review provides a summary of the application of furazan-containing molecules in medicinal chemistry and drug development programs from analysis of both patent and academic literature. Emphasis is placed on programs that reached clinical or preclinical stages of development. The examples provided herein describe the pharmacology and biological activity of furazan derivatives with comparative data provided where possible for other heterocyclic groups and pharmacophores commonly used in medicinal chemistry.

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