Synthesis, Structure and Antifungal Activity of New 3-[(5-Aryl-1,3,4-oxadiazol-2-yl)methyl]benzo[d]thiazol-2(3H)-ones

Abstract

A series of new 3-[(5-aryl-1,3,4-oxadiazol-2-yl)methy])benzo[d]thiazol-2(3H)-ones were synthesized by reaction of (5-substituted-2-oxobenzothiazolin-3-yl)-acetohydrazide with various aromatic acids in POCl3 under reflux conditions. The structures of the title compounds were confirmed by 1H-NMR, 13C-NMR, IR, MS and elemental analysis. Furthermore, the structure of compound 4i was determined by single-crystal X-ray diffraction. The preliminary bioassy results indicated that some of them showed moderate inhibition activity against Colletotrichum orbiculare, Botrytis cinerea and Rhizoctonia solani.

Straightforward Synthesis of N-Methyl-4-(pin)B-2(3H)-benzothiazol-2-one: A Promising Cross-Coupling Reagent

“…Representative studies of 1 include the following: (1) tiaramide as a characteristic and useful anti-allergic drug [2]; (2) benazoline as a useful selective herbicide [3]; (3) chlobenthiazone as a potent agrochemical fungicide [4,5]; and (4) natural mevashuntin as a unique metabolite of an hydroxymethylglutaryl-CoA (HMG-CoA) reductase inhibitor [6] and as an efficient target for total synthesis [7]. Other notable pharmaceuticals have also been reported [8][9][10][11].…”

“…Representative studies of 1 include the following: (1) tiaramide as a characteristic and useful anti-allergic drug [2]; (2) benazoline as a useful selective herbicide [3]; (3) chlobenthiazone as a potent agrochemical fungicide [4,5]; and (4) natural mevashuntin as a unique metabolite of an hydroxymethylglutarylCoA (HMG-CoA) reductase inhibitor [6] and as an efficient target for total synthesis [7]. Other notable pharmaceuticals have also been reported [8][9][10][11] Compared with simple unsubstituted, 6-chlorinated, and 5-acyl (or alkyl)-substituted N-alkyl-2(3H)-benzothiazol-2-ones, the synthesis of more inaccessible 4-substituted analogues is quite limited due to the three stereocongested contiguous substituents on the 4,8,9-positions. To the best of our knowledge, only three compounds containing the 4-substituted N-alkyl-2(3H)-benzothiazol-2-one structure have been reported: benazoline [3], chlobenthiazone [4,5], and mevashuntin [6] (Figure 1).…”

Synthesis and Antifungal Activity of Novel 3-[(5-Benzylthio- 1,3,4-oxadiazol-2-yl)methyl]benzo[d]thiazol- (oxazol)-2(3H)-ones

“…鉴于此, 根据活性亚结构拼 接原理, 兼具苯并噻(噁)唑、1,3,4-噁二唑和硫醚三者结 构单元的化合物有望具有良好农药活性. 在前期工作中, 课题组设计合成了一系列苯并噻唑 联 1,3,4-噁二唑化合物, 生测结果表明其具有一定杀菌 活性 [21] . 为寻找具有更佳杀菌活性的农药先导化合物, 1 结果与讨论 …”

Convenient synthesis and characterization of some novel benzothiazolone-based Schiff bases as potential pharmaceutically active agents

“…24 Furthermore, In recent years, several potentially useful bioactive substances based on the benzothiazolone nucleus have been extensively studied because of their wide range of pharmacological activities. [25][26][27][28][29] , and were reported as potential analgesic and anti-inflammatory agents. [30][31][32][33][34] All the facts discussed above and in continuation of our research on nitrogen and sulfur containing heterocycles, inspired us to develop an efficient and simple synthesis of a new series of benzothiazolone derived Schiff's base derivatives (Figure 1), which may exert potent pharmacological action.…”