(2S)-2-amino-N-[2-(1,3-benzothiazol-2-ylamino)-2-oxoethyl]-3-phenylpropanamide;hydrochloride | 1414969-71-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S)-2-amino-N-[2-(1,3-benzothiazol-2-ylamino)-2-oxoethyl]-3-phenylpropanamide;hydrochloride
• CAS: 1414969-71-3
• 化学式: C₁₈H₁₈N₄O₂S*ClH
• 分子量: 390.893
• InChiKey: WNUZYWIOQOIXBK-ZOWNYOTGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.34
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  125
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  tert-butyl 2-(benzo[d]thiazol-2-ylamino)-2-oxoethylcarbamate 在 盐酸 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 9.0h， 生成 (2S)-2-amino-N-[2-(1,3-benzothiazol-2-ylamino)-2-oxoethyl]-3-phenylpropanamide;hydrochloride
  参考文献：
  名称：

  Synthesis of retinoid enhancers based on 2-aminobenzothiazoles for anti-cancer therapy

  摘要：

  Indole-3-amides and dipeptides were produced from 2-aminobenzothiazoles using the PyBop peptide coupling reagent. These analogues were tested in anti-cancer cell viability assays against SH-SY5Y neuroblastoma and MDA-MB-231 breast adenocarcinoma cell lines, and were found to exhibit cytotoxic activities at concentrations ranging from 0.1 to 20 mu M. These compounds were also found to act additively with a low dosage of 13-cis-retinoic acid in neuroblastoma cells. Then, using neuroblastoma cells transfected to stably overexpress the RAR beta(2) gene, a SAR was developed for the indole-3-amides. Real-time PCR was also used to demonstrate their RAR beta(2) agonistic activity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.09.035

文献信息

• Synthesis of retinoid enhancers based on 2-aminobenzothiazoles for anti-cancer therapy
  作者：Christopher R. Gardner、Belamy B. Cheung、Jessica Koach、David StC. Black、Glenn M. Marshall、Naresh Kumar

  DOI：10.1016/j.bmc.2012.09.035

  日期：2012.12

  Indole-3-amides and dipeptides were produced from 2-aminobenzothiazoles using the PyBop peptide coupling reagent. These analogues were tested in anti-cancer cell viability assays against SH-SY5Y neuroblastoma and MDA-MB-231 breast adenocarcinoma cell lines, and were found to exhibit cytotoxic activities at concentrations ranging from 0.1 to 20 mu M. These compounds were also found to act additively with a low dosage of 13-cis-retinoic acid in neuroblastoma cells. Then, using neuroblastoma cells transfected to stably overexpress the RAR beta(2) gene, a SAR was developed for the indole-3-amides. Real-time PCR was also used to demonstrate their RAR beta(2) agonistic activity. (C) 2012 Elsevier Ltd. All rights reserved.