(E)-2-(benzo[d]thiazol-2-yl)-3-(5-nitrofuran-2-yl)acrylonitrile | 134407-86-6

• 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: (E)-2-(benzo[d]thiazol-2-yl)-3-(5-nitrofuran-2-yl)acrylonitrile
• 英文别名: 2-(1,3-Benzothiazol-2-YL)-3-(5-nitro-2-furyl)acrylonitrile；(E)-2-(1,3-benzothiazol-2-yl)-3-(5-nitrofuran-2-yl)prop-2-enenitrile
• CAS: 134407-86-6
• 化学式: C₁₄H₇N₃O₃S
• 分子量: 297.294
• InChiKey: JESQZERTWSMDEP-VQHVLOKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-氨基苯硫醇 在 溶剂黄146 、 potassium hydroxide 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 2.0h， 生成 (E)-2-(benzo[d]thiazol-2-yl)-3-(5-nitrofuran-2-yl)acrylonitrile
  参考文献：
  名称：

  Mycobacterium tuberculosis lysine-ɛ-aminotransferase a potential target in dormancy: Benzothiazole based inhibitors

  摘要：

  MTB lysine-epsilon-aminotransferase (LAT) was found to play a crucial role in persistence and antibiotic tolerance. LAT serves as a potential target in the management of latent tuberculosis. In present work we attempted to derivatize the benzothiazole lead identified through high throughput virtual screening of Birla Institute of Technology and Science in house database. For Structure activity relationship purpose 22 derivatives were synthesized and characterized. Among synthesized compounds, eight compounds were found to be more efficacious in terms of LAT inhibition when compared to lead compound (IC50 10.38 +/- 1.21 mu M). Compound 22 exhibits bactericidal action against nutrient starved Mycobacterium tuberculosis (MTB). It also exhibits significant activity in nutrient starvation model (2.9 log folds) and biofilm model (2.3 log folds). 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.03.053

文献信息

• Structure–activity relationships of novel heteroaryl-acrylonitriles as cytotoxic and antibacterial agents
  作者：Franciszek Sączewski、Agnieszka Stencel、Andrzej M. Bieńczak、Karolina A. Langowska、Martin Michaelis、Władysław Werel、Rafał Hałasa、Przemyslaw Reszka、Patrick J. Bednarski

  DOI：10.1016/j.ejmech.2007.11.017

  日期：2008.9

  Eighteen new 2,6-disubstituted acrylonitriles and two new (benzimidazol-1-yl)-acetamide derivatives were prepared and screened for antibacterial and cytotoxic activities on 12 human cancer cell lines. Based on the lead structure 2-(benzimidazol-2-yl)-3-(5-nitrothiophen-2-yl) acrylonitrile it was found that placement of methyl groups at the 5,6 positions of the benzimidazole ring lead to a 3-fold increase in overall cytotoxic activity. Replacing the nitrothiophene for pyridine reduced cytotoxic activity as did replacing the nitro group for a methoxy group. Cytotoxic activity was only slightly reduced when the benzimidazole ring was replaced by a imidazo[4,5-b]pyridine or a benzthiazole ring but replacement by benzoxazole led to a substantial decrease in activity. Moving the acrylonitrile group from position 2 to position 1 of the benzimidazole ring also resulted in moderately active compounds. (Benzimidazol-1-yl)acetamides showed only modest activity. The structure-activity relationships found in the cytotoxicity studies are mirrored in the results of the antibacterial experiments. (C) 2007 Elsevier Masson SAS. All rights reserved.
• Kada, Rudolf; Ilavsky, Dusan; Goljer, Igor, Collection of Czechoslovak Chemical Communications, 1991, vol. 56, # 2, p. 418 - 424
  作者：Kada, Rudolf、Ilavsky, Dusan、Goljer, Igor、Gaher, Peter

  DOI：——

  日期：——
• KADA, RUDOLF;ILAVSKY, DUSAN;GOLJER, IGOR;GAHER, PETER, COLLECT. CZECHOSL. CHEM. COMMUN. , 56,(1991) N, C. 418-424
  作者：KADA, RUDOLF、ILAVSKY, DUSAN、GOLJER, IGOR、GAHER, PETER

  DOI：——

  日期：——
• Mycobacterium tuberculosis lysine-ɛ-aminotransferase a potential target in dormancy: Benzothiazole based inhibitors
  作者：Rudraraju Srilakshmi Reshma、Variam Ullas Jeankumar、Nidhi Kapoor、Shalini Saxena、Karyakulam Andrews Bobesh、Astakala Rishi Vachaspathy、Pappachan E. Kolattukudy、Dharmarajan Sriram

  DOI：10.1016/j.bmc.2017.03.053

  日期：2017.5

  MTB lysine-epsilon-aminotransferase (LAT) was found to play a crucial role in persistence and antibiotic tolerance. LAT serves as a potential target in the management of latent tuberculosis. In present work we attempted to derivatize the benzothiazole lead identified through high throughput virtual screening of Birla Institute of Technology and Science in house database. For Structure activity relationship purpose 22 derivatives were synthesized and characterized. Among synthesized compounds, eight compounds were found to be more efficacious in terms of LAT inhibition when compared to lead compound (IC50 10.38 +/- 1.21 mu M). Compound 22 exhibits bactericidal action against nutrient starved Mycobacterium tuberculosis (MTB). It also exhibits significant activity in nutrient starvation model (2.9 log folds) and biofilm model (2.3 log folds). 2017 Elsevier Ltd. All rights reserved.