N-(2-氯乙基)-1,3-苯并噻唑-2-胺 | 75105-02-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 中文名称: N-(2-氯乙基)-1,3-苯并噻唑-2-胺
• 英文名称: N-(2-chloroethyl)-1,3-benzothiazol-2-amine
• 英文别名: 2-β-chloroethylaminobenzothiazole；N-(2-chloroethyl)benzo[d]thiazol-2-amine
• CAS: 75105-02-1
• 化学式: C₉H₉ClN₂S
• 分子量: 212.703
• InChiKey: BYWDTRLKZBJCBO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  53.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2-氯乙基)-1,3-苯并噻唑-2-胺 在 potassium carbonate 作用下， 以 氯仿 为溶剂， 以47%的产率得到2,3-dihydroimidazo[2,1-b]benzothiazole
  参考文献：
  名称：

  Unexpected reactivity of annulated 3H-benzothiazol-2-ylideneamines as an acyl transfer catalyst

  摘要：

  Catalytic ability of annulated 3H-benzothiazol-2-ylideneamines and 1H-pyridin-2-ylideneamines for acylation of alcohols was investigated and 3,4-dihydro-2H-9-thia-1,4a-diazafluorene (2b) was found to be an extremely effective catalyst, the reaction with which was faster than that with DMAP. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.04.109
• 作为产物：
  描述：

  2-氯苯并噻唑 在 氯化亚砜 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 N-(2-氯乙基)-1,3-苯并噻唑-2-胺
  参考文献：
  名称：

  Unexpected reactivity of annulated 3H-benzothiazol-2-ylideneamines as an acyl transfer catalyst

  摘要：

  Catalytic ability of annulated 3H-benzothiazol-2-ylideneamines and 1H-pyridin-2-ylideneamines for acylation of alcohols was investigated and 3,4-dihydro-2H-9-thia-1,4a-diazafluorene (2b) was found to be an extremely effective catalyst, the reaction with which was faster than that with DMAP. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.04.109

文献信息

• Synthesis and In Vitro Antitumor Activity of Novel Fluorine Containing Pyrazoles and Pyrazolines
  作者：Ashish Sharma、Tabreskhan Pathan、Rhea Mohan、C. S. Ramaa

  DOI：10.2174/157018011797200812

  日期：2011.11.1

  Novel fluorine-containing pyrazolines (2a-2g) and pyrazoles (5a-5e) were synthesized and evaluated for their cytotoxicity in vitro in a panel of four human cancer cell lines using Sulforhodamine B (SRB) assay. Though the compounds showed varying degrees of cytotoxicity in different cell lines, it was noteworthy that the 4H pyrazoles (5a-5e) were distinguished by their potent and selective action against MCF7 breast cancer cell line.

  研究人员合成了新型含氟吡唑（2a-2g）和吡唑（5a-5e），并使用磺基罗丹明 B（SRB）测定法对它们在体外四种人类癌细胞系中的细胞毒性进行了评估。尽管这些化合物在不同的细胞系中表现出不同程度的细胞毒性，但值得注意的是，4H 吡唑（5a-5e）对 MCF7 乳腺癌细胞系具有强效的选择性作用。
• Synthesis and binding assays of novel 3,3-dimethylpiperidine derivatives with various lipophilicities as σ1 receptor ligands
  作者：Savina Ferorelli、Carmen Abate、Maria P. Pedone、Nicola A. Colabufo、Marialessandra Contino、Roberto Perrone、Francesco Berardi

  DOI：10.1016/j.bmc.2011.10.023

  日期：2011.12

  Starting from two carbocyclic analogs, a series of 3,3-dimethylpiperidine derivatives was prepared and tested in radioligand binding assays at sigma(1) and sigma(2) receptors, and at Delta(8)-Delta(7) sterol isomerase (SI) site. The novel compounds mostly bear heterocyclic rings or bicyclic nucleus of differing lipophilicities. Compounds 18a and 19a,b demonstrated the highest sigma(1) affinity (K-i = 0.14-0.38 nM) with a good selectivity versus sigma(2) binding. Among them, 18a had the lowest C log D value (3.01) and only 19b was selective versus SI too. Generally, it was observed that more planar and hydrophilic heteronuclei conferred a decrease in affinity for both sigma receptor subtypes. (C) 2011 Elsevier Ltd. All rights reserved.
• Makovei, G. L.; Ushakov, V. G.; Bagin, V. K., Russian Journal of Applied Chemistry, 1989, vol. 62, p. 1245 - 1250
  作者：Makovei, G. L.、Ushakov, V. G.、Bagin, V. K.、Fedorenko, G. V.、Krasovskii, A. N.

  DOI：——

  日期：——
• Unexpected reactivity of annulated 3H-benzothiazol-2-ylideneamines as an acyl transfer catalyst
  作者：Megumi Kobayashi、Sentaro Okamoto

  DOI：10.1016/j.tetlet.2006.04.109

  日期：2006.6

  Catalytic ability of annulated 3H-benzothiazol-2-ylideneamines and 1H-pyridin-2-ylideneamines for acylation of alcohols was investigated and 3,4-dihydro-2H-9-thia-1,4a-diazafluorene (2b) was found to be an extremely effective catalyst, the reaction with which was faster than that with DMAP. (c) 2006 Elsevier Ltd. All rights reserved.