(5-Methyl-benzo[d]isothiazol-3-yl)-acetic acid hydrazide | 287487-97-2

• 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: (5-Methyl-benzo[d]isothiazol-3-yl)-acetic acid hydrazide
• 英文别名: 2-(5-Methyl-1,2-benzothiazol-3-yl)acetohydrazide；2-(5-methyl-1,2-benzothiazol-3-yl)acetohydrazide
• CAS: 287487-97-2
• 化学式: C₁₀H₁₁N₃OS
• 分子量: 221.283
• InChiKey: ZEWAIBCOHWCYKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  96.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,4-二硝基苯甲醛 、 (5-Methyl-benzo[d]isothiazol-3-yl)-acetic acid hydrazide 在 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以85%的产率得到N-[(E)-(2,4-dinitrophenyl)methylideneamino]-2-(5-methyl-1,2-benzothiazol-3-yl)acetamide
  参考文献：
  名称：

  Synthesis and antiproliferative activity of benzo[d]isothiazole hydrazones

  摘要：

  Several benzo[d]isothiazole hydrazones have been evaluated for their potential antiretroviral activity. Since a number of these compounds were found to be inactive against viruses, but showed cytotoxicity at micromolar concentrations against the human CD4(+) lymphocytes (MT-4) that were used to support HIV-1 growth, they were further tested for antiproliferative activity. The compounds resulted as being cytotoxic for MT-4 cells and new derivatives which were rationally designed and synthesized, were tested for antiproliferative activity against several leukaemia and solid, tumour cell lines. In addition, these compounds were evaluated against "normal" cell lines. Compound 2h proved to be the most active compound and the fragment -CO-NH-N=CH-2-hydroxyphenyl was identified as being very important for biological activity, suggesting intramolecular, hydrogen bond formation or favourable mutual disposition between two important centres in the pharmacophore. H-1-NMR spectra have been explained with the support of a conformational analysis. (c) 2006 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.01.010
• 作为产物：
  描述：

  (5-methyl-benzo[d]isothiazol-3-yl)-acetic acid ethyl ester 在 一水合肼 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 (5-Methyl-benzo[d]isothiazol-3-yl)-acetic acid hydrazide
  参考文献：
  名称：

  具有潜在抗菌活性的新型 1,2-苯异噻唑衍生物的实验和计算亲脂性指数的合成和相关性

  摘要：

  由环状（1和4）或非环状（2、3和5）1合成了具有潜在抗菌活性的五个系列新型腙（1a-m、2a-m、3a-m、4a-m、5a-m）， 2-苯并异噻唑基酰肼和表征。适当的酰肼与醛缩合得到设计的化合物。使用带有不同疏水取代基的醛，并设计了五个系列，以便同系物之间的疏水性也不同。保留参数通过 HPLC 测量，使用去活的烷基键合硅胶柱和不同的洗脱液系统（甲醇 - 水性缓冲液，乙腈 - 水）。将疏水性色谱参数 (log k') 与通过测量正辛醇和水之间的溶质分配 (log P) 提供的参数以及理论分配系数进行比较，由碎片法计算并根据实验值进行缩放。报告和讨论了不同疏水性指数之间的相关性

  DOI：

  10.1002/(sici)1521-4184(20005)333:5<135::aid-ardp135>3.0.co;2-u

文献信息

• Hydrazones of 1,2-benzisothiazole hydrazides: synthesis, antimicrobial activity and QSAR investigations
  作者：Paola Vicini、Franca Zani、Pietro Cozzini、Irini Doytchinova

  DOI：10.1016/s0223-5234(02)01378-8

  日期：2002.7

  series of hydrazones of 1,2-benzisothiazole hydrazides 1a-m, 2a-m, 3a-m, 4a-m, 5a-m as well as their cyclic (1 and 4) and acyclic (2, 3 and 5) 1,2-benzisothiazole parent hydrazides, were synthesised and evaluated as antibacterial and antifungal agents. All of the 2-amino-1,2-benzisothiazol-3(2H)-one derivatives, belonging to series I and IV, showed a good antibacterial activity against Gram positive

  1,2-苯并噻唑唑酰肼1a-m，2a-m，3a-m，4a-m，5a-m的一系列hydr以及它们的环状（1和4）和非环状（2、3和5）1合成了2-2-苯并噻唑的母体酰肼，并作为抗菌剂和抗真菌剂进行了评估。属于系列I和IV的所有2-amino-1,2-benzisothiazol-3（2H）-one衍生物均显示出对革兰氏阳性细菌的良好抗菌活性。他们中的大多数也对酵母有活性。化合物1和4与1l一起被证明是最有效的化合物。采用二维-QSAR分析进行定量构效关系（QSAR）研究，以发现所研究化合物的不同实验或计算物理化学参数之间的相关性。进行了3D-QSAR研究，
• Anti-HIV evaluation of benzo[d]isothiazole hydrazones
  作者：Paola Vicini、Matteo Incerti、Paolo La Colla、Roberta Loddo

  DOI：10.1016/j.ejmech.2008.05.030

  日期：2009.4

  The synthesis and the anti-HIV-1 activity of novel benzo[d]isothiazole hydrazones are reported. Target compounds tested in MT-4 cells cultures for their anti-HIV properties against wild type HIV-1 and HIV strains carrying clinically relevant mutations (EFV(R), Y181C and K103/Y181C) showed good activity against wild type HIV-1 and against the EFVR mutant. In terms of SAR the relevant result was that, in the class of benzisothiazole hydrazones, the benzo[d]isothiazol-3(2H)-one moiety (compounds 1 and 4) is an essential structural requirement for the anti-retroviral activity. (C) 2008 Elsevier Masson SAS. All rights reserved.
• Synthesis and Correlations between Experimental and Calculated Lipophilic Indices of New 1,2-Benzisothiazole Derivatives with Potential Antimicrobial Activity
  作者：Paola Vicini、Emilia Fisicaro、Maria Teresa Lugari

  DOI：10.1002/(sici)1521-4184(20005)333:5<135::aid-ardp135>3.0.co;2-u

  日期：2000.5

  Five series of new hydrazones (1a—m, 2a—m, 3a—m, 4a—m, 5a—m) with potential antimicrobial activity were synthesized from cyclic (1 and 4) or acyclic (2, 3 and 5) 1,2‐benzisothiazolylhydrazides and characterized. Condensation of the appropriate hydrazide with aldehydes afforded the designed compounds. Aldehydes carrying different hydrophobic substituents were used and the five series were designed so

  由环状（1和4）或非环状（2、3和5）1合成了具有潜在抗菌活性的五个系列新型腙（1a-m、2a-m、3a-m、4a-m、5a-m）， 2-苯并异噻唑基酰肼和表征。适当的酰肼与醛缩合得到设计的化合物。使用带有不同疏水取代基的醛，并设计了五个系列，以便同系物之间的疏水性也不同。保留参数通过 HPLC 测量，使用去活的烷基键合硅胶柱和不同的洗脱液系统（甲醇 - 水性缓冲液，乙腈 - 水）。将疏水性色谱参数 (log k') 与通过测量正辛醇和水之间的溶质分配 (log P) 提供的参数以及理论分配系数进行比较，由碎片法计算并根据实验值进行缩放。报告和讨论了不同疏水性指数之间的相关性
• Synthesis and antiproliferative activity of benzo[d]isothiazole hydrazones
  作者：Paola Vicini、Matteo Incerti、Irini A. Doytchinova、Paolo La Colla、Bernadetta Busonera、Roberta Loddo

  DOI：10.1016/j.ejmech.2006.01.010

  日期：2006.5

  Several benzo[d]isothiazole hydrazones have been evaluated for their potential antiretroviral activity. Since a number of these compounds were found to be inactive against viruses, but showed cytotoxicity at micromolar concentrations against the human CD4(+) lymphocytes (MT-4) that were used to support HIV-1 growth, they were further tested for antiproliferative activity. The compounds resulted as being cytotoxic for MT-4 cells and new derivatives which were rationally designed and synthesized, were tested for antiproliferative activity against several leukaemia and solid, tumour cell lines. In addition, these compounds were evaluated against "normal" cell lines. Compound 2h proved to be the most active compound and the fragment -CO-NH-N=CH-2-hydroxyphenyl was identified as being very important for biological activity, suggesting intramolecular, hydrogen bond formation or favourable mutual disposition between two important centres in the pharmacophore. H-1-NMR spectra have been explained with the support of a conformational analysis. (c) 2006 Elsevier SAS. All rights reserved.