(4E)-4-[(2-(1,3-苯并噻唑-2-基)肼基)亚甲基]-2-羟基环己-2,5-二烯-1-酮

• 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: (4E)-4-[(2-(1,3-苯并噻唑-2-基)肼基)亚甲基]-2-羟基环己-2,5-二烯-1-酮
• 英文名称: (E)-4-((2-(benzo[d]thiazol-2-yl)hydrazono)methyl)benzene-1,2-diol
• 英文别名: 4-{(E)-[2-(1,3-benzothiazol-2-yl)hydrazinylidene]methyl}benzene-1,2-diol；4-[(E)-(1,3-benzothiazol-2-ylhydrazinylidene)methyl]benzene-1,2-diol
• 化学式: C₁₄H₁₁N₃O₂S
• 分子量: 285.326
• InChiKey: YCXDDQDRAORENL-OVCLIPMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  106
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-肼基苯并噻唑 、 3,4-二羟基苯甲醛 以 乙醇 为溶剂， 反应 4.0h， 生成 (4E)-4-[(2-(1,3-苯并噻唑-2-基)肼基)亚甲基]-2-羟基环己-2,5-二烯-1-酮
  参考文献：
  名称：

  2-苯并噻唑腙衍生物的超分子固态结构、势能面及体外抗增殖作用评价

  摘要：

  2-肼基苯并噻唑与水杨醛、3,4-二羟基苯甲醛、2,4-二羟基苯甲醛、2,5-二羟基苯甲醛、2,3-二羟基苯甲醛、2-羟基-1-萘甲醛、2-甲氧基-1-的原位缩合反应萘醛、4-甲氧基-1-萘醛和6-甲氧基-2-萘醛产生9 种腙席夫碱（分别为L1-L9），通过元素分析、IR 和NMR 光谱对其进行鉴定和表征。四种席夫碱（L1、L7-L9）的晶体和分子结构已通过单晶 X 射线衍射法确定，证实了 L1 的亚氨基形式和 L7-L9 化合物的氨基互变异构形式。分子结构分析还证实，报告的化合物是 E 异构体，相对于 exo C = N 亚氨基键。氨基互变异构体的Nhydrazino-H基团形成Nhydrazino-H···Nthiazolyl分子间氢键使分子形成R22(8)环，而L1的亚氨基互变异构体通过Nthiazolyl-H···Nhydrazino型形成C(4)无限螺旋链分子间氢键。甲氧基（L7

  DOI：

  10.1007/s11224-016-0856-0

文献信息

• Synthesis and Antitumor Evaluation of (E)-2-Benzothiazole Hydrazones
  作者：Antonio Francisco Nogueira、Elisa Carvalho Azevedo、Vitor Francisco Ferreira、Ana Jersia Araujo、Evelyne Alves dos Santos、Claudia Pessoa、Leticia Veras Costa-Lotufo、Raquel Carvalho Montenegro、Manoel Odorico de Moraes、Thatyana Rocha Alves Vasconcelos

  DOI：10.2174/157018010792062740

  日期：2010.10.1

  A series of eleven (E)-2-benzothiazole hydrazones were synthesized and evaluated for their in vitro anticancer activities against three neoplastic cancer cells: HL-60 (leukemia), MDAMB-435 (breast) and HCT-8 (colon). Two of them, 3e and 3f, showed good cytotoxicity activity for HL-60. The results also demonstrated that compound 3f seems to be selective to HL-60 cell line, appearing as a good prototype for an antileukemia lead molecule.

  合成了一系列11种（E）-2-苯并噻唑肼，并评估了它们对三种肿瘤癌细胞的体外抗癌活性：HL-60（白血病）、MDAMB-435（乳腺癌）和HCT-8（结肠）。其中，3e和3f对HL-60显示出良好的细胞毒性活性。结果还表明，化合物3f似乎对HL-60细胞系具有选择性，表现为一个优良的抗白血病先导分子原型。
• Polymerizable compound, polymerizable composition, polymer, and optically anisotropic material
  申请人：ZEON CORPORATION

  公开号：US10647794B2

  公开（公告）日：2020-05-12

  The invention provides a polymerizable compound of formula (I), polymerizable composition, polymer, and optically anisotropic article capable of obtaining an optical film having a low melting point, excellent solubility, being manufactured at low cost, and of uniform polarized light conversion across a broad wavelength region. In formula (I): Y1 to Y6 are independently a chemical single bond, —O—, —O—C(═O)—, —C(═O)—O—; G1 and G2 are independently a divalent C1-C20 aliphatic group; Z1 and Z2 are independently a C2-C10 alkenyl group substituted with a halogen atom; Ax is a C2-C30 organic group that includes at least one aromatic ring of an aromatic hydrocarbon ring or an aromatic hetero ring; Ay is H, a C1-C20 alkyl group, a C2-C20 alkenyl group, a C3-C12 cycloalkyl group; A1 is a trivalent aromatic group; A2 and A3 are independently a divalent C6-C30 aromatic group; and Q1 is H, or a C1-C6 alkyl group.

  本发明提供了一种可聚合的式(I)化合物、可聚合组合物、聚合物和光学各向异性制品，能够获得熔点低、溶解性好、制造成本低、在宽波长区域内偏振光转换均匀的光学薄膜。在式 (I) 中Y1 至 Y6 独立地为化学单键、-O-、-O-C(═O)-、-C(═O)-O-；G1 和 G2 独立地为二价 C1-C20 脂肪族基团；Z1 和 Z2 独立地为被卤原子取代的 C2-C10 烯基；Ax 是 C2-C30 有机基团，其中包括至少一个芳香烃环或芳香杂环；Ay 是 H、C1-C20 烷基、C2-C20 烯基、C3-C12 环烷基；A1 是三价芳香基团；A2 和 A3 独立地是二价 C6-C30 芳香基团；Q1 是 H 或 C1-C6 烷基。
• Synthesis and anticancer activity of (E)-2-benzothiazole hydrazones
  作者：Eric B. Lindgren、Monique A. de Brito、Thatyana R.A. Vasconcelos、Manuel O. de Moraes、Raquel C. Montenegro、Julliane D. Yoneda、Kátia Z. Leal

  DOI：10.1016/j.ejmech.2014.08.039

  日期：2014.10

  Benzothiazole hydrazones have been synthesized and evaluated for their in vitro antiproliferative activity against three human cancer cell lines: HL-60 (leukemia), MDAMB-435 (breast) and HCT-8 (colon). The good cytotoxicity for the three cancer cell lines and theoretical profile of compounds 3o and 3p pointed them as promising lead molecules for anticancer drug design. (c) 2014 Elsevier Masson SAS. All rights reserved.
• POLYMERIZABLE COMPOUND, POLYMERIZABLE COMPOSITION, POLYMER, AND OPTICALLY ANISOTROPIC MATERIAL
  申请人：Zeon Corporation

  公开号：EP2703385B1

  公开（公告）日：2017-09-20
• Synthesis, antioxidant and cytoprotective evaluation of potential antiatherogenic phenolic hydrazones. A structure–activity relationship insight
  作者：Corinne Vanucci-Bacqué、Chantal Carayon、Corinne Bernis、Caroline Camare、Anne Nègre-Salvayre、Florence Bedos-Belval、Michel Baltas

  DOI：10.1016/j.bmc.2014.05.034

  日期：2014.8

  A novel series of hydrazones derived from substituted benzaldehydes have been synthesized as potential antiatherogenic agents. Several methods were used for exploring their antioxidant and cytoprotective properties, such as their scavenging effect on 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical, the inhibition of superoxide anion (O₂(·-)) generation and the measurement of cell-induced low-density lipoprotein oxidation (monitored by the formation of TBARS). The cytoprotective efficacy was also evaluated by measuring the cell viability (monitored by the MTT assay) in the presence of cytotoxic oxidized LDL. In this report, we discuss the relationship between the chemical structure of phenolic hydrazones and their antioxidant and cytoprotective activities, for subsequent application as antiatherogenic agents. This SAR study confirms that the phenolic frame is not the only prerequisite for antioxidant activity and N-methylbenzothiazole hydrazone moiety magnifies the dual required properties in two most interesting derivatives.