2-chloro-N-(6-thiocyanatobenzo[d]thiazol-2-yl)acetamide | 1338431-88-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 2-chloro-N-(6-thiocyanatobenzo[d]thiazol-2-yl)acetamide
• 英文别名: [2-[(2-chloroacetyl)amino]-1,3-benzothiazol-6-yl] thiocyanate
• CAS: 1338431-88-1
• 化学式: C₁₀H₆ClN₃OS₂
• 分子量: 283.762
• InChiKey: LKJPRMPYNVCUEI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  119
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-chloro-N-(6-thiocyanatobenzo[d]thiazol-2-yl)acetamide 、 (5Z)-5-[4-(dimethylamino)benzylidene]-1,3-thiazolidine-2,4-dione 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以59%的产率得到(E)-2-(5-(4-(dimethylamino)benzylidene)-2,4-dioxothiazolidin-3-yl)-N-(6-thiocyanatobenzo[d]thiazol-2-yl) acetamide
  参考文献：
  名称：

  Synthesis of some new 2-amino-6-thiocyanato benzothiazole derivatives bearing 2,4-thiazolidinediones and screening of their in vitro antimicrobial, antitubercular and antiviral activities

  摘要：

  A series of new (E)-2-(5-substituted benzylidene-2,4-dioxothiazolidin-3-yl)-N-(6-thiocyanatobenzo[d]thiazol-2-yl)acetamides have been synthesized. The structures of title compounds have been confirmed by elemental analyses, IR, H-1 NMR and C-13 NMR spectral data. All the synthesized compounds were tested for antimicrobial and antitubercular activity and also were evaluated for anti-HIV activity. Several compounds exhibited good antibacterial activity (9, 15, 27 and 31 against E. coli; 8 and 28 against S. aureus); some displayed good antifungal activity (4, 7, 13, 19, 23, 24, 25 and 31 against C. albicans). Compounds 14, 20 and 22 showed good antitubercular activity. Unfortunately, none of the compounds were found to be active against anti-HIV-1. However, one of the intermediates, the 2-chloro-N-(6-thiocyanatobenzo[d]thiazol-2-yl)acetamide, showed significant cytotoxicity for MT-4 cells (CC50 = 8.0 A mu M).

  DOI：

  10.1007/s00044-015-1358-0
• 作为产物：
  描述：

  苯胺 在 溴 、 sodium carbonate 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.75h， 生成 2-chloro-N-(6-thiocyanatobenzo[d]thiazol-2-yl)acetamide
  参考文献：
  名称：

  Synthesis of some new 2-amino-6-thiocyanato benzothiazole derivatives bearing 2,4-thiazolidinediones and screening of their in vitro antimicrobial, antitubercular and antiviral activities

  摘要：

  A series of new (E)-2-(5-substituted benzylidene-2,4-dioxothiazolidin-3-yl)-N-(6-thiocyanatobenzo[d]thiazol-2-yl)acetamides have been synthesized. The structures of title compounds have been confirmed by elemental analyses, IR, H-1 NMR and C-13 NMR spectral data. All the synthesized compounds were tested for antimicrobial and antitubercular activity and also were evaluated for anti-HIV activity. Several compounds exhibited good antibacterial activity (9, 15, 27 and 31 against E. coli; 8 and 28 against S. aureus); some displayed good antifungal activity (4, 7, 13, 19, 23, 24, 25 and 31 against C. albicans). Compounds 14, 20 and 22 showed good antitubercular activity. Unfortunately, none of the compounds were found to be active against anti-HIV-1. However, one of the intermediates, the 2-chloro-N-(6-thiocyanatobenzo[d]thiazol-2-yl)acetamide, showed significant cytotoxicity for MT-4 cells (CC50 = 8.0 A mu M).

  DOI：

  10.1007/s00044-015-1358-0

文献信息

• New 2-benzylsulfanyl-nicotinic acid based 1,3,4-oxadiazoles: Their synthesis and biological evaluation
  作者：Navin B. Patel、Amit C. Purohit、Dhanji P. Rajani、Rosa Moo-Puc、Gildardo Rivera

  DOI：10.1016/j.ejmech.2012.12.055

  日期：2013.4

  electrophiles (E+), such as haloacetate and haloalkyl groups, were performed to get target compounds 6a–j. Compounds were characterized by NMR, mass, IR spectra and C, H, N analyses. All compounds were evaluated for their antimicrobial and antimycobacterial activities; selected analogs were screened for their anticancer activity on 60 tumor cell lines at single dose 1.00−5 M. Unfortunately, none of the compounds

  从关键中间体5-（2-苄基硫烷基-吡啶- ）合成了一系列新的5-（2-苄基硫烷基-吡啶-3-基）-2-（取代）-硫烷基-1,3,4-恶二唑6a – j。 3-（基）-3 H- [1,3,4]恶二唑-2-硫酮5。进行了不同亲电子试剂（E +）的亲核取代反应，例如卤代乙酸酯和卤代烷基，从而得到目标化合物6a – j。通过NMR，质谱，IR光谱和C，H，N分析来表征化合物。对所有化合物的抗微生物和抗分枝杆菌活性进行了评估。筛选选定的类似物以单剂量1.00 -5对60种肿瘤细胞系的抗癌活性 M.不幸的是，没有一种化合物对60种人类肿瘤细胞系显示出显着的抗肿瘤活性。然而，与氨苄西林相比，具有苯并噻唑部分（分别为12.5和25μg/ ml）的化合物6g和6f对大肠杆菌表现出令人鼓舞的活性。与利福平相比，分别带有三唑和吗啉的化合物6d，6j显示出有希望的抗结核活性（25μg/ ml）。
• [EN] 6-(ALKYL- OR CYCLOALKYL-TRIAZOLOPYRIDAZINE-SULFANYL) BENZOTHIAZOLE DERIVATIVES: PREPARATION, APPLICATION AS MEDICAMENTS AND USE AS MET INHIBITORS<br/>[FR] DERIVES DE 6-(ALKYL- OU CYCLOALKYL-TRIAZOLOPYRIDAZINE-SULFANYL) BENZOTHIAZOLES: PREPARATION, APPLICATION COMME MEDICAMENTS ET UTILISATION COMME INHIBITEURS DE MET
  申请人：SANOFI AVENTIS

  公开号：WO2011121223A1

  公开（公告）日：2011-10-06

  L'invention concerne les nouveaux produits de formule (I); avec R1 représente alkyle, cycloalkyle ou cycloalkylalkyle; Rb représente un atome d'hydrogène ou bien atome de fluor W représente H; alkyle, cycloalkyle, hétérocycloalkyle ou COR avec R représente cycloalkyle, hétérocycloalkyle, alkyle; alcoxy, -O-hétérocycloalkyle; ou NHR2 avec R2 représente H, cycloalkyle, hétérocycloalkyle ou alkyle; tous éventuellement substitués; ces produits étant sous toutes les formes isomères et les sels, à titre de médicaments notamment comme inhibiteurs de MET.