Selective thromboxane synthetase inhibitors. 3. 1H-imidazol-1-yl-substituted benzo[b]furan-, benzo[b]thiophene-, and indole-2- and -3-carboxylic acids.

doi:10.1021/JM00159A012

Paper

Selective thromboxane synthetase inhibitors. 3. 1H-imidazol-1-yl-substituted benzo[b]furan-, benzo[b]thiophene-, and indole-2- and -3-carboxylic acids.

Published Sep 1, 1986 · P. Cross, R. Dickinson, M. Parry

Journal of medicinal chemistry

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13

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0

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Abstract

The preparation of a series of 1H-imidazol-1-yl-substituted benzo[b]furan-, benzo[b]thiophene-, and indolecarboxylic acids is described. Most of the compounds were potent inhibitors of TxA2 synthetase in vitro, and the distance between the imidazole and carboxylic acid groups was found to be important for optimal potency. The most potent compound in vivo was 6-(1H-imidazol-1-ylmethyl)-3-methylbenzo[b]thiophene-2-carboxylic acid (71), which, in conscious dogs, showed a similar profile of activity to that of dazoxiben (1).

In Vitro Study

Study Snapshot

The compounds prepared in this study show potential as potent inhibitors of thromboxane synthetase, with 6-(1H-imidazol-1-ylmethyl)-3-methylbenzo[b]thiophene-2-carboxylic acid (71), showing a similar activity

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Selective thromboxane synthetase inhibitors. 3. 1H-imidazol-1-yl-substituted benzo[b]furan-, benzo[b]thiophene-, and indole-2- and -3-carboxylic acids.

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References

Citations

Classification models and SAR analysis on thromboxane A2 synthase inhibitors by machine learning methods

Model_4D, a deep neural network with 67 bits MACCS fingerprints, effectively predicts bioactivity of thromboxane A2 synthase inhibitors, with aromatic nitrogenous heterocyclic groups improving their bioactivity.

Thia-Bridged Triarylamine Hetero[4]Helicenes: Regioselective Synthesis and Functionalization

Thia-bridged triarylamine hetero[4]helicenes show promise as organic electronic materials, and regioselective preparation of asymmetric derivatives offers potential for applications in organic electronics.

Design and synthesis of pyrrolobenzodiazepine-gallic hybrid agents as p53-dependent and -independent apoptogenic signaling in melanoma cells.

PBD-GA hybrid agents show potential as chemotherapeutic agents for melanoma with activated p53 or mutant p53, causing cell death through p53-dependent and -independent pathways.

DC-81-enediyne induces apoptosis of human melanoma A375 cells: involvement of the ROS, p38 MAPK, and AP-1 signaling pathways

DC-81-enediyne induces apoptosis in human melanoma A375 cells through increased calcium and reactive oxygen species generation, p38 phosphorylation, and enhanced ATF-2/AP-1 expressions.

Synthesis and structure-activity relationship of 1H-indole-3-carboxylic acid pyridine-3-ylamides: a novel series of 5-HT2C receptor antagonists.

The novel series of 1H-indole-3-carboxylic acid pyridine-3-ylamides show high affinity and selectivity for 5-HT2C receptor, with 15k showing the highest affinity and selectivity over other serotonin and dopamine receptors.