(4-benzothiazol-2-ylpiperazin-1-yl)acetic acid hydrazide | 1266359-97-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: (4-benzothiazol-2-ylpiperazin-1-yl)acetic acid hydrazide
• 英文别名: 2-[4-(1,3-Benzothiazol-2-yl)piperazin-1-yl]acetohydrazide
• CAS: 1266359-97-0
• 化学式: C₁₃H₁₇N₅OS
• 分子量: 291.377
• InChiKey: SESFNHZUJACEQZ-UHFFFAOYSA-N

物化性质

• 熔点：
  186-188 °C
• 密度：
  1.344±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3-二氯苯甲酸 、 (4-benzothiazol-2-ylpiperazin-1-yl)acetic acid hydrazide 在 2,6-二甲基吡啶 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以75%的产率得到2,3-dichlorobenzoic acid N-[2-(4-benzothiazol-2-ylpiperazin-1-yl)acetyl]hydrazide
  参考文献：
  名称：

  Synthesis and an angiolytic role of novel piperazine–benzothiazole analogues on neovascularization, a chief tumoral parameter in neoplastic development

  摘要：

  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.

  DOI：

  10.1016/j.bioorg.2016.02.006
• 作为产物：
  描述：

  2-氯苯并噻唑 在 碳酸氢钠 、 一水合肼 作用下， 以 乙醇 为溶剂， 反应 29.0h， 生成 (4-benzothiazol-2-ylpiperazin-1-yl)acetic acid hydrazide
  参考文献：
  名称：

  Synthesis and an angiolytic role of novel piperazine–benzothiazole analogues on neovascularization, a chief tumoral parameter in neoplastic development

  摘要：

  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.

  DOI：

  10.1016/j.bioorg.2016.02.006

文献信息

• Synthesis, in vitro Antiproliferative and Anti-HIV Activity of New Derivatives of 2-Piperazino-1,3-benzo[d]thiazoles
  作者：Yaseen A. Al-Soud、Haitham H. Al-Sa’doni、Sadeekah O. W. Saber、Reem H. M. Al-Shaneek、Najim A. Al-Masoudi、P. La Colla

  DOI：10.1515/znb-2010-1113

  日期：2010.11.1

  }-(het)arenecarboxamides 4a - l, sulfonamide derivatives 8a - i as well as benzothiazole-containing N1-(2-oxoethyl)-N1-arylthioureas 9a - c have been synthesized. Compounds 4a - l and 9a were evaluated, in vitro, for their antiproliferative activity against a large panel of human tumor-derived cell lines. Compounds 4l and 9a were the most potent analogs in this series, showing remarkable effects on

  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。
• 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.