Synthesis and pharmacological evaluation of 2-substituted benzo[b]thiophenes as anti-inflammatory and analgesic agents
| Autor: | Seham El-Batran, Mohamed A. A. Radwan, Issa M. I. Fakhr, Omar M. E. Abd El‐Salam, Siham M. El-Shenawy |
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| Rok vydání: | 2009 |
| Předmět: |
Pain Threshold
Carbamate medicine.medical_treatment Hydrazine Anti-Inflammatory Agents Pain Thiophenes Carrageenan Hydrazide Chemical synthesis Mice Piroxicam Structure-Activity Relationship chemistry.chemical_compound Drug Discovery medicine Animals Edema Organic chemistry Aspartate Aminotransferases Stomach Ulcer Acetic Acid Pharmacology Semicarbazide Chemistry Organic Chemistry Alanine Transaminase General Medicine Isocyanate Rats Liver Azide Curtius rearrangement |
| Zdroj: | European Journal of Medicinal Chemistry. 44:1718-1725 |
| ISSN: | 0223-5234 |
| DOI: | 10.1016/j.ejmech.2008.02.034 |
| Popis: | An efficient method for trapping isocyanate 4, generated from the Curtius rearrangement, with ethyl alcohol to afford the carbamate 5 is reported. 5-Nitrobenzo[b]thiophene-2-carboxylic acid 1 is converted to the corresponding hydrazide 2 by the reaction with hydrazine hydrate and then to the azide 3 with nitrous acid, followed by thermal rearrangement, cooling, and trapping in one pot reaction. The carbamate 5 is treated with hydrazine hydrate to afford the desired, Zileuton analogue, 4-(5-nitrobenzo[b]thiophene-2-yl)semicarbazide 6. Also the reactivity of hydrazide 2 towards some carboxyaldehydes and phenylisothiocyanate afforded the corresponding carbohydrazides 7, 8 and phenylthiosemicarbazide 9, respectively. Compounds 9, 2 and 6, respectively, were more potent as anti-inflammatory and anti-nociceptive agents. |
| Databáze: | OpenAIRE |
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