7-methyl-[1,3]thiazolo[3,2-a]-benzimidazole-3(2H)-one | 79938-36-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 7-methyl-[1,3]thiazolo[3,2-a]-benzimidazole-3(2H)-one
• 英文别名: 7-methyl-[1,3]thiazolo[3,2-a]benzimidazol-3(2H)-one；7-methyl[1,3]thiazolo[3,2-a]benzimidazol-3(2H)-one；6-Methyl-[1,3]thiazolo[3,2-a]benzimidazol-1-one
• CAS: 79938-36-6
• 化学式: C₁₀H₈N₂OS
• 分子量: 204.252
• InChiKey: JLYNOUVTMBWRNE-UHFFFAOYSA-N

物化性质

• 熔点：
  192-195 °C(Solv: ethanol (64-17-5))
• 沸点：
  401.4±38.0 °C(Predicted)
• 密度：
  1.51±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  60.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-methyl-[1,3]thiazolo[3,2-a]-benzimidazole-3(2H)-one 在 镍 作用下， 以 乙酸乙酯 为溶剂， 以54.7%的产率得到(9ci)-1-乙酰基-5-甲基-1H-苯并咪唑
  参考文献：
  名称：

  Tanaka, Kenjiro; Shimazaki, Michiko; Murakami, Yasuoki, Chemical and pharmaceutical bulletin, 1982, vol. 30, # 8, p. 2714 - 2722

  摘要：

  DOI：
• 作为产物：
  描述：

  [(6-甲基-1H-苯并咪唑-2-基)硫基]乙酸 在 吡啶 、 乙酸酐 作用下， 反应 0.17h， 生成 7-methyl-[1,3]thiazolo[3,2-a]-benzimidazole-3(2H)-one
  参考文献：
  名称：

  Antihelminthic activity of some newly synthesized 5(6)-(un)substituted-1H-benzimidazol-2-ylthioacetylpiperazine derivatives

  摘要：

  Piperazine derivatives of 5(6)-substituted-(1H-benzimidazol-2-ylthio)acetic acids were synthesized by using two methods and studied for antihelminthic activity.The antiparasitic screening showed that compounds 18-24 exhibited higher activity against Trichinella spiralis in vitro in comparison to methyl 5-(propylthio)-1H-benzimidazol-2-yl-carbamate (albendazole). Most active were compounds 2-({2-[4-(4-chlorophenyl)piperazin-1-yl]-2-oxoethyl}thio)-1H-benzimidazole 21 and 2-{[2-oxo-2-(4-benzhydrylpiperazin-1-yl)ethyl]thio}-5(6)-methyl-1(H)-benzimidazole 19 as well as 2-({2-[4-(4-chlorophenyl)piperazin-1-yl]-2-oxoethyl}thio)-5(6)-methyl-](H)-benzimidazole 23 with efficacy of 96.0%, 98.4% and 100%, respectively.The tested derivatives 15-19 and 20-23 were less active against Syphacia obvelata in vivo than albendazole and exhibited the same efficacy as piperazine, but in twice lower concentration. Compounds 2-({2-[4-(4-chlorophenyl)piperazin-1-yl]-2-oxoethyl}thio)-1H-benzimidazole 21, 1,4-bis[(5(6)-methyl-l(H)-benzimidazol-2-ylthio)acetyl]piperazine 17 and 2-({2-[4-(4-chlorophenyl)piperazin-1-yl]-2-oxoethyl)thio)-5(6)-methyl- 1(H)-benzimidazole 23 had higher efficacies of 73%, 76%, and 77%, respectively. (c) 2006 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.07.005

文献信息

• Cyclization of ((4- or 5-substituted-2-benzimidazolyl)thio)acetic acids. Isolation and identification of two possible isomers of substituted thiazolo(3,2-a)benzimidazol-3(2H)-one.
  作者：KENJIRO TANAKA、MICHIKO INO、YASUOKI MURAKAMI

  DOI：10.1248/cpb.29.1876

  日期：——

  Cyclizations of [(5-substituted-2-benzimidazolyl) thio] acetic acid (2a-e) to the corresponding thiazolo [3, 2-a] benzimidazol-3 (2H)-one (5 and 6) were successfully carried out by heating 2a-e in Dowtherm A or Ac2O/pyridine, and gave the two possible isomers (5a-e and 6a-e) in a ratio of nearly 1 : 1 in all cases. Separation of 5 and 6 was successfully carried out, and their structures (namely, the direction of cyclization) were suggested on the basis of the NMR spectra. Dowtherm A was more effective than Ac2O/pyridine, particularly for the cyclization of [(5-nitro-2-benzimidazolyl) thio] acetic acid (2a), which had been reported not to be cyclized with other reagents. Similar cyclization of [(4-methyl-2-benzimidazolyl) thio] acetic acid (2f) preferentially gave 8-methylthiazolo [3, 2-a]-benzimidazol-3 (2H)-one (6f).

  将[(5-取代-2-苯并咪唑基)硫代]乙酸(2a-e)加热环化成相应的噻唑并[3,2-a]苯并咪唑-3(2H)-酮(5和6)的反应已经成功实施，使用Dowtherm A或Ac2O/吡啶作为溶剂，并且在这两种情况下，均以近似1:1的比例得到了两种可能的异构体(5a-e和6a-e)。成功分离了5和6，并根据NMR谱图推断出了它们的结构，即环化的方向。Dowtherm A比Ac2O/吡啶更为有效，尤其是对于[(5-硝基-2-苯并咪唑基)硫代]乙酸(2a)，此前有报道指出它不能用其他试剂环化。类似的环化反应中，[(4-甲基-2-苯并咪唑基)硫代]乙酸(2f)优先形成了8-甲基噻唑并[3,2-a]苯并咪唑-3(2H)-酮(6f)。
• Synthesis and antitrichinellosis activity of some 2-substituted-[1,3]thiazolo[3,2-a]benzimidazol-3(2H)-ones
  作者：Anelia Ts. Mavrova、Kamelya K. Anichina、Dimitar I. Vuchev、Jordan A. Tsenov、Magdalena S. Kondeva、Mitka K. Micheva

  DOI：10.1016/j.bmc.2005.06.046

  日期：2005.10

  Some new thiazolo[3,2-a]benzimidazolone derivatives were synthesized using two methods. The structures of the synthesized compounds were proved by means of IR, (1)H NMR and mass spectral data. Ab initio computations were performed in order to determine the electronic structure and geometry of the investigated molecules and to compare it to the geometry of albendazole. Biologically, experiments in vitro

  使用两种方法合成了一些新的噻唑并[3,2-a]苯并咪唑酮衍生物。借助IR，（1）H NMR和质谱数据证明了合成化合物的结构。为了确定所研究分子的电子结构和几何形状并将其与阿苯达唑的几何形状进行比较，进行了从头算。在生物学上，完成了体外和体内实验，以鉴定获得的噻唑基苯并咪唑啉酮对旋毛虫的功效。对于浓度为100mg / kg mw的化合物4a和4c，化合物4a-c在旋毛虫病的肠道阶段的有效性为100％，在肌肉阶段的有效性为88％和80％。
• Tautomerism and isomerism in some antitrichinellosis active benzimidazoles: Morphological study in polarized light, quantum chemical computations
  作者：Kameliya Anichina、Anelia Mavrova、Denitsa Yancheva、Jordan Tsenov、Rasho Dimitrov

  DOI：10.1016/j.molstruc.2017.08.073

  日期：2017.12

  Abstract The morphology of the crystal structure of some antitrichinellosis active benzimidazole derivatives including (1 H -benzimidazol-2-ylthio)acetic acids, [1,3]thiazolo[3,2- a ]benzimidazol-3(2 H )-ones, 1 H -benzimidazol-2-ylthioacetylpiperazines and starting 2-mercapto benzimidazoles, was studied by the use of Polarized Light Microscopy (PLM). Characterization of the crystal phase was complimented

  摘要 一些抗旋毛虫病活性苯并咪唑衍生物包括（1 H-苯并咪唑-2-基硫基）乙酸、[1,3]噻唑并[3,2-a]苯并咪唑-3(2 H)-酮的晶体结构形态， 1 H-苯并咪唑-2-基硫代乙酰哌嗪和起始2-巯基苯并咪唑，通过使用偏振光显微镜(PLM)进行了研究。通过差示扫描量热分析 (DSC) 和光谱数据对晶相进行表征。进行 DFT 计算是为了研究合成化合物的质子互变异构和分子的几何形状。PLM 观察到 5 或 6-甲基-（1H-苯并咪唑-2-基硫基）乙酸 6 中每一种的一种不同类型的晶体结构 - 树枝状和针状结构。化合物 14 , 在苯并咪唑环中含有甲基取代基的结晶也分为两相；而对于未取代的化合物 13，不会发生相分离。研究了两种溶剂-氯仿和乙醇对化合物14的相分离和晶体结构形成的影响。形态学研究表明，6-甲基-[1,3]噻唑并[3,2-a]苯并咪唑-3(2H)-酮在乙酸酐存在下，在吡啶介质中环化生成了6-甲基-[1
• Phase-Transfer Catalyzed Alkylation and Acylation of 2-Mercapto-5-Methyl-1<i>H</i>-Benzimidazole
  作者：Ali Kh. Khalil

  DOI：10.1080/10426500601059433

  日期：2007.2.15

  Solid/liquid phase-transfer catalyzed alkylation and acylation of 2-mercaptobenzimidazole at 25°C by different organohalogen reagents in the presence of tetrabutylammonium bromide as a catalyst underwent, exclusively, S-monoalkylation and N-monoacylation or S-and N-dialkylation, cycloalkylation, and S-and N-diacyla-tion depending on the nature of alkylating and acylating agents.

  在四丁基溴化铵作为催化剂的存在下，2-巯基苯并咪唑在 25°C 的固/液相转移催化烷基化和酰化，仅经历了 S-单烷基化和 N-单酰化或 S-和 N-二烷基化，环烷基化和 S-和 N-二酰化取决于烷基化剂和酰化剂的性质。
• 피부미백 활성을 갖는 신규 화합물 및 이의 의학적 용도
  申请人：Pusan National University Industry-University Cooperation Foundation 부산대학교 산학협력단(220040044843) BRN ▼621-82-06530

  公开号：KR101488583B1

  公开（公告）日：2015-02-03

  본 발명은 피부미백 활성을 갖는 신규 화합물 및 이의 의학적 용도에 관한 것으로, 본 발명에 따른 화합물들은 티로시나아제를 억제하는 피부미백 활성을 지니므로 피부미백용 약학조성물, 화장료조성물 또는 건강기능식품으로 사용될 수 있다.

  该发明涉及具有皮肤美白活性的新化合物及其医学用途，根据该发明，这些化合物具有抑制酪氨酸酶的皮肤美白活性，因此可用作皮肤美白药物配方、化妆品配方或保健食品。