4-(5-chlorobenzothiazol-2-yl)-N,N-dimethylaniline | 887701-43-1

• 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: 4-(5-chlorobenzothiazol-2-yl)-N,N-dimethylaniline
• 英文别名: 4-(5-chloro-1,3-benzothiazol-2-yl)-N,N-dimethylaniline
• CAS: 887701-43-1
• 化学式: C₁₅H₁₃ClN₂S
• 分子量: 288.801
• InChiKey: JTJKNVJLPWBSFH-UHFFFAOYSA-N

物化性质

• 沸点：
  442.5±51.0 °C(Predicted)
• 密度：
  1.303±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  44.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  对二甲氨基苯甲醛 、 2-氨基-4-氯苯硫醇 在 sodium metabisulfite 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 以68%的产率得到4-(5-chlorobenzothiazol-2-yl)-N,N-dimethylaniline
  参考文献：
  名称：

  Synthesis, and In Vitro and In Silico α-Glucosidase Inhibitory Studies of 5-Chloro-2-Aryl Benzo[d]thiazoles

  摘要：

  Twenty-five derivatives of 5-chloro-2-aryl benzo[d]thiazole (1-25) were synthesized and evaluated for their alpha-glucosidase (S. cerevisiae EC 3.2.1.20) inhibitory activity in vitro. Among them eight compounds showed potent activity with IC50 values between 22.1 +/- 0.9 and 136.2 +/- 5.7 mu M, when compared with standard acarbose (IC50 = 840 +/- 1.73 mu M). The most potent compounds 4, 9, and 10 showed IC50 values in the range of 22.1 +/- 0.9 to 25.6 +/- 1.5 mu M. Compounds 2, 5, 11, and 19 showed IC50 values within the range of 40.2 +/- 0.5 to 60.9 +/- 2.0 mu M. Compounds 1 and 3 were also found to be good inhibitors with IC50 values 136.2 +/- 5.7 and 104.8 +/- 9.9 lM, respectively. Their activities were compared with alpha-glucosidase inhibitor drug acarbose (standard) (IC50 = 840 +/- 1.73 mu M). The remaining compounds were inactive. Structure-activity relationships (SAR) have also been established. Kinetics studies indicated compounds 2, 3, 10, 19, and 25 to be non-competitive, while 1, 5, 9, and 11 as competitive inhibitors of alpha-glucosidase enzyme. All the active compounds (1-5, 9-11, and 19) were also found to be non-cytotoxic, in comparison to the standard drug i.e., doxorubicin (IC50 = 0.80 +/- 0.12 mu M) in MTT assay. Furthermore, molecular interactions of active compounds with the enzyme binding sites were predicted through molecular modeling studies. (C) 2018 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2018.02.013

文献信息

• Synthesis of Benzothiazoles through Copper-Catalyzed One-Pot Three-Component Reactions with Use of Sodium Hydrosulfide as a Sulfur Surrogate
  作者：Namjin Park、Yumi Heo、Manian Rajesh Kumar、Yong Kim、Kwang Ho Song、Sunwoo Lee

  DOI：10.1002/ejoc.201101773

  日期：2012.4

  Copper-catalyzed one-pot three-component reactions of 2-iodoanilines, aldehydes, and NaSH·n H2O afford benzothiazoles in good yields. When CuCl was employed as a catalyst in the absence of a ligand, a variety of aromatic aldehydes and substituted 2-iodoanilines reacted with NaSH·n H2O to produce the corresponding 2-arylbenzothiazoles in 70–98 % yields. The copper catalyst plays a key role in C–S bond

  铜催化的 2-碘苯胺、醛和 NaSH·n H2O 的一锅三组分反应以良好的收率提供苯并噻唑。当在没有配体的情况下使用 CuCl 作为催化剂时，各种芳香醛和取代的 2-碘苯胺与 NaSH·n H2O 反应生成相应的 2-芳基苯并噻唑，产率为 70-98%。铜催化剂在 NaSH·n H2O 和由 2-碘苯胺和醛缩合形成的芳基碘之间形成 C-S 键中起关键作用。研究发现，NaSH·n H2O 在苯并噻唑的形成过程中起硫替代物和氧化剂的作用。
• Methods of screening bifunctional molecules for modulated pharmacokinetic properties
  申请人：Gestwicki E. Jason

  公开号：US20070054348A1

  公开（公告）日：2007-03-08

  Methods for screening bifunctional molecules of a drug of interest for modulated pharmacokinetic properties are provided. The subject methods include combining in a reaction mixture a metabolizer of the drug of interest, a reporter of activity of the metabolizer; and a bifunctional compound of the drug of interest. Signal from the reporter is then-evaluated to determine whether the bifunctional compound has a modulated pharmacokinetic property as compared to a free drug control. Also provided are kits and devices for practicing the subject methods of the invention.
• Synthesis, and In Vitro and In Silico α-Glucosidase Inhibitory Studies of 5-Chloro-2-Aryl Benzo[d]thiazoles
  作者：Shazia Shah、Arshia、Kulsoom Javaid、Humaira Zafar、Khalid Mohammed Khan、Ruqaiya Khalil、Zaheer Ul-Haq、Shahnaz Perveen、M. Iqbal Choudhary

  DOI：10.1016/j.bioorg.2018.02.013

  日期：2018.8

  Twenty-five derivatives of 5-chloro-2-aryl benzo[d]thiazole (1-25) were synthesized and evaluated for their alpha-glucosidase (S. cerevisiae EC 3.2.1.20) inhibitory activity in vitro. Among them eight compounds showed potent activity with IC50 values between 22.1 +/- 0.9 and 136.2 +/- 5.7 mu M, when compared with standard acarbose (IC50 = 840 +/- 1.73 mu M). The most potent compounds 4, 9, and 10 showed IC50 values in the range of 22.1 +/- 0.9 to 25.6 +/- 1.5 mu M. Compounds 2, 5, 11, and 19 showed IC50 values within the range of 40.2 +/- 0.5 to 60.9 +/- 2.0 mu M. Compounds 1 and 3 were also found to be good inhibitors with IC50 values 136.2 +/- 5.7 and 104.8 +/- 9.9 lM, respectively. Their activities were compared with alpha-glucosidase inhibitor drug acarbose (standard) (IC50 = 840 +/- 1.73 mu M). The remaining compounds were inactive. Structure-activity relationships (SAR) have also been established. Kinetics studies indicated compounds 2, 3, 10, 19, and 25 to be non-competitive, while 1, 5, 9, and 11 as competitive inhibitors of alpha-glucosidase enzyme. All the active compounds (1-5, 9-11, and 19) were also found to be non-cytotoxic, in comparison to the standard drug i.e., doxorubicin (IC50 = 0.80 +/- 0.12 mu M) in MTT assay. Furthermore, molecular interactions of active compounds with the enzyme binding sites were predicted through molecular modeling studies. (C) 2018 Elsevier Inc. All rights reserved.