(4-benzothiazol-2-ylpiperazin-1-yl)acetic acid ethyl ester | 232263-19-3

• 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: (4-benzothiazol-2-ylpiperazin-1-yl)acetic acid ethyl ester
• 英文别名: Ethyl 2-[4-(1,3-benzothiazol-2-yl)piperazin-1-yl]acetate；ethyl 2-[4-(1,3-benzothiazol-2-yl)piperazin-1-yl]acetate
• CAS: 232263-19-3
• 化学式: C₁₅H₁₉N₃O₂S
• 分子量: 305.401
• InChiKey: RRWUNWHLYNXNTG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  73.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4-benzothiazol-2-ylpiperazin-1-yl)acetic acid ethyl ester 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 8.0h， 以84%的产率得到(4-benzothiazol-2-ylpiperazin-1-yl)acetic acid hydrazide
  参考文献：
  名称：

  2-Piperazino-1,3-benzo[d]thiazoles 新衍生物的合成、体外抗增殖和抗 HIV 活性

  摘要：

  一系列 N-{2-oxo-2-[4-(1,3-benzothiazol-2-yl)piperazin-1-yl]}-(het)arenecarboxamides 4a - l、磺酰胺衍生物 8a - i 以及已合成含苯并噻唑的 N1-(2-氧乙基)-N1-芳基硫脲 9a-c。体外评价化合物4a-1和9a对一大组人肿瘤衍生细胞系的抗增殖活性。化合物4l和9a是该系列中最有效的类似物，对人脾B淋巴细胞样细胞（WIL-2NS）和人急性B淋巴细胞白血病（CCRF-SB）细胞系（4l：CC50 = 5.1和7.3）显示出显着影响分别为 μM）和化合物 5 对抗 CCRF-SB 细胞系，CC50 = 2.3 μM。这些化合物是进一步开发的主要候选物。化合物 6 - 7a - i 被筛选为抗 HIV-1 和 HIV-2 的抑制剂，没有发现任何活性。

  DOI：

  10.1515/znb-2010-1113
• 作为产物：
  描述：

  2-氯苯并噻唑 在 sodium carbonate 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 16.0h， 生成 (4-benzothiazol-2-ylpiperazin-1-yl)acetic acid ethyl ester
  参考文献：
  名称：

  Small molecules enhance functional O-mannosylation of Alpha-dystroglycan

  摘要：

  Alpha-dystroglycan (alpha-DG), a highly glycosylated receptor for extracellular matrix proteins, plays a critical role in many biological processes. Hypoglycosylation of alpha-DG results in various types of muscular dystrophies and is also highly associated with progression of majority of cancers. Currently, there are no effective treatments for those devastating diseases. Enhancing functional O-mannosyl glycans (FOG) of alpha-DG on the cell surfaces is a potential approach to address this unmet challenge. Based on the hypothesis that the cells can up-regulate FOG of alpha-DG in response to certain chemical stimuli, we developed a cell-based high-throughput screening (HTS) platform for searching chemical enhancers of FOG of alpha-DG from a large chemical library with 364,168 compounds. Sequential validation of the hits from a primary screening campaign and chemical works led to identification of a cluster of compounds that positively modulate FOG of alpha-DG on various cell surfaces including patient-derived myoblasts. These compounds enhance FOG of alpha-DG by almost ten folds, which provide us powerful tools for O-mannosylation studies and potential starting points for the development of drug to treat dystroglycanopathy. (c) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.11.011

文献信息

• Synthesis and an angiolytic role of novel piperazine–benzothiazole analogues on neovascularization, a chief tumoral parameter in neoplastic development
  作者：Mohammed Al-Ghorbani、G.S. Pavankumar、P. Naveen、Prabhu Thirusangu、B.T. Prabhakar、Shaukath Ara Khanum

  DOI：10.1016/j.bioorg.2016.02.006

  日期：2016.4

  A novel series of benzoic acid N'-[2-(4-benzothiazol-2-yl-piperazin-1-yl)-acetyl]-hydrazides 6a-j were synthesized and characterized by IR, H-1, C-13 NMR, elemental and mass spectral analyses. The in-vitro cytotoxicity and cell viability assay of the synthesized compounds 6a-j were evaluated against Dalton's lymphoma ascites (DLA) cells. Our results showed that compound 6c with a bromo group on phenyl ring has showed promising antiproliferative efficacy. Further investigation of compound 6c on in-vivo treatment model depicts the increased tumor suppression through inhibition of angiogenesis. (C) 2016 Elsevier Inc. All rights reserved.