Nichtsteroidale Entzündungshemmer, 17. Mitt.¹) 4.5‐Bis(4‐methoxyphenyl)‐2‐arylthio‐azole mit antiphlogistischer Wirkung

Abstract

Es werden die Synthesen von 4.5-Bis(4-methoxyphenyl)-2-arylthio-imidazolen, - Antiinflammatory Agents, XVII: 4.5-Bis-(4-methoxypbenyl)-2-(arylthio)azoles with Antiinfianunatory ActivityThe syntheses of 4,5-bis(4-methoxyphenyl)-2-(arylthio)imidazoles, -thiazoles and -oxazoles are described and their antiinflammatory activities are compared. Thioethers, sulfoxides, and sulfones of the phenyl, 4-fluorophenyl, and 2-thienyl derivatives were investigated. The oxazole derivatives show almost no antiphlogistic activities, thiazoles have a mean efficacy, and the imidazoles are the most active compounds. In the acute test, the imidazoles were not ulcerogenic.Wir berichteten bereits uber die guten entziindungshemmenden Eigenschaften und die geringe Ulcerogenitat der 4.5-Bis(4-methoxyphenyl)-2-cycloalkylthio-imidazole 1-4'). In Weiterftihrung dieser Arbeiten sollte gepriift werden, ob sich die therapeutischen Qualitaten erhohen und die Nebenwirkungen weiter erniedrigen lassen, wenn der Akylthiorest in 2-Position des Imidazolringes durch Arylthioreste ersetzt wird. Dariiber hinaus sollten die zu diesen Verbindungen isosteren Thiazole und Oxazole untersucht werden. Die dazu analog substituierten 4.5-und 4.6-Bis(4-methoxyphenyl)-2-arylthio-pyrimidine zeigten keine nennenswerten entziindungshemmenden Aktivitaten2).Wir synthetisierten zunachst die Bis-4.5(4-methoxyphenyl)-irnidazole mit Phenylthio-5,4-Fluorphenylthio-6 und 2-Thienylthiorest 7 in 2-Position und anschlieBend die isosteren Thiazole 8, 9, 10 und die Oxazole 11, 12, l3 priiften auf entziindungshemmende Eigenschaften. Dabei bezogen wir die aus den Thioethern leicht zuganglichen Sulfoxide und Sulfone in unsere Untersuchungen ein (Schema 1).Die Imidazolderivate 5,6,7 lieBen sich uber das literaturbekannte Mercaptoimidazol H3) darstellen (Schema 2).

Synthesis and biological evaluation of sulfonamide thiazole and benzothiazole derivatives as antimicrobial agents

“…Anti-inflammatory, analgesic, and antipyretic activities for some thiazolyl and benzothiazolyl derivatives are also known. 7,8 On the other hand, sulfonamides have a variety of biological activities such as antibacterial, [9][10][11] insulin releasing, 12 carbonic anhydrase inhibitory, 13,14 anti-inflammatory, 15 and antitumor 16 activities. These findings encouraged us to explore the synthesis of sulfonamides containing thiazole/benzothiazole moieties and to examine their antibacterial and antifungal properties.…”

Computer aided prediction of biological activity spectra: Evaluating versus known and predicting of new activities for thiazole derivatives

“…To evaluate the applicability of the approach to the thiazole derivatives, the results of prediction are compared to experimental data for some compounds from the set, studied as 3,4,5,6,7,8,9,10,11,12,14,15,17,18,19,20,26,27,28,29 non-steroid antiinflammatory (78 compounds); local anaesthetics (6 compounds); antioxidants (5 compounds) tests. These data are given in Table II. In the experiment the compound is considered as being active if its potency is no less than the potency of the appropriate reference drug (the experimental errors are taken into account).…”

“…Anti-inflammatory, analgesic, antipyretic activities for some thiazolyl and benzoisothiazolyl derivatives are also known [9,10]. The screening tests for these compounds have been chosen on the basis of certain researchers' purposes.…”

Pharmacological activities of some new polycyclic triazolopyrazolopyridazine derivatives

“…In our previous work, some of polycyclic hetero-system derivatives were studied as 5␣-reductase inhibitors, antiviral, anti-tumor [1], aromatase and quinone reductase-2 inhibitors for chemoprevention of cancer [2], anti-inflammatory, analgesic and antipyretic activities [3][4][5][6][7][8]. Recent studies have shown the synthesis of some new azole candidates as antimicrobial and anticancer agents [9][10][11][12][13].…”