3-(6-bromohexyl)-1,3-thiazolidine-2,4-dione | 316363-18-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 3-(6-bromohexyl)-1,3-thiazolidine-2,4-dione
• 英文别名: 3-(6-bromohexyl)thiazolidine-2,4-dione；3-(6-Bromohexyl)-2,4-thiazolidinedione
• CAS: 316363-18-5
• 化学式: C₉H₁₄BrNO₂S
• 分子量: 280.186
• InChiKey: RJDKHOSWKMFCKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  62.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(6-bromohexyl)-1,3-thiazolidine-2,4-dione 在 盐酸 作用下， 以 乙醇 、 氯仿 、 水 为溶剂， 反应 22.0h， 生成 [N-(6-(2,4-dioxo-1,3-thiazolidin-3-yl)hexyl)]ammonium chloride
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of novel 2,4-thiazolidinedione derivatives as histone deacetylase inhibitors targeting liver cancer cell line

  摘要：

  As a part of an ongoing effort to find alternate chemotherapeutic agents for hepatocellular carcinoma, we herein, report the design and synthesis of two novel compounds targeting histone deacetylase (HDAC) with 2,4-thiazolidinedione as zinc chelating group. Further, we demonstrate that these compounds show cytotoxicity that parallels their ability to inhibit HDACs activity in human liver cancer cell line HepG2. The findings obtained in this study indicate that 2,4-thiazolidinedione group may be utilized successfully to inhibit HDAC activity with future potential for lead optimization by chemical derivatization of active compound, N-(6-(2,4-dioxothiazolidin-3- yl)hexyl) benzenesulfonamide.

  DOI：

  10.1007/s00044-011-9623-3
• 作为产物：
  描述：

  2,4-噻唑烷二酮 、 1,6-二溴己烷 在 三乙胺 作用下， 以 乙腈 为溶剂， 以70%的产率得到3-(6-bromohexyl)-1,3-thiazolidine-2,4-dione
  参考文献：
  名称：

  Benzimidazole compounds and drugs containing the same

  摘要：

  一种苯并咪唑化合物或其盐，其对巨噬细胞的形成具有抑制作用，并可作为预防或治疗动脉硬化的药物的有效成分，其由公式（I）表示： 其中，R1代表苯环上的功能基团，选自包括氢原子、卤素原子、低级烷基和低级烷氧基的组；R2代表氢原子、烷基或酰基；R3代表含有氮原子和Z的环上的功能基团；Z代表形成一个5或6元环的二价基团；L代表C4-C8烷基链或由(CH2CH2O)nCH2CH2表示的乙烯氧链连接基团，其中n代表1或2；X代表氧或硫。

  公开号：

  US06593323B1

文献信息

• Benzimidazole compounds and drugs containing the same
  申请人：Fuji Photo Film Co., Ltd.

  公开号：US06593323B1

  公开（公告）日：2003-07-15

  A benzimidazole compound or a salt thereof which has an inhibitory action of forming of macrophages and is useful as an active ingredient of a medicament for preventive and/or therapeutic treatment of arteriosclerosis, which is represented by the formula (I): wherein, R1 represents a functional group on the benzene ring selected from the group consisting of hydrogen atom, a halogen atom, a lower alkyl group and a lower alkoxy group; R2 represents hydrogen atom, an alkyl group or an acyl group; R3 represents a functional group on the ring containing the nitrogen atom and Z; Z represents a divalent group which forms a 5- or 6-membered ring; L represents a C4-C8 alkylene group or an ethyleneoxy linking group represented by (CH2CH2O)nCH2CH2 wherein n represents 1 or 2; and X represents O or S.

  一种苯并咪唑化合物或其盐，其对巨噬细胞的形成具有抑制作用，并可作为预防或治疗动脉硬化的药物的有效成分，其由公式（I）表示： 其中，R1代表苯环上的功能基团，选自包括氢原子、卤素原子、低级烷基和低级烷氧基的组；R2代表氢原子、烷基或酰基；R3代表含有氮原子和Z的环上的功能基团；Z代表形成一个5或6元环的二价基团；L代表C4-C8烷基链或由(CH2CH2O)nCH2CH2表示的乙烯氧链连接基团，其中n代表1或2；X代表氧或硫。
• BENZIMIDAZOLE COMPOUNDS AND DRUGS CONTAINING THE SAME
  申请人：FUJI PHOTO FILM CO., LTD.

  公开号：EP1201664A1

  公开（公告）日：2002-05-02

  A benzimidazole compound or a salt thereof which has an inhibitory action of forming of macrophages and is useful as an active ingredient of a medicament for preventive and/or therapeutic treatment of arteriosclerosis, which is represented by the formula (I): wherein, R1 represents a functional group on the benzene ring selected from the group consisting of hydrogen atom, a halogen atom, a lower alkyl group and a lower alkoxy group; R2 represents hydrogen atom, an alkyl group or an acyl group; R3 represents a functional group on the ring containing the nitrogen atom and Z; Z represents a divalent group which forms a 5- or 6-membered ring; L represents a C4-C8 alkylene group or an ethyleneoxy linking group represented by (CH2CH2O)nCH2CH2 wherein n represents 1 or 2; and X represents O or S.

  一种苯并咪唑化合物或其盐，具有抑制巨噬细胞形成的作用，可作为预防和/或治疗动脉硬化的药物的活性成分，由式(I)表示： 其中，R1 代表苯环上的官能团，选自氢原子、卤素原子、低级烷基和低级烷氧基组成的组；R2 代表氢原子、烷基或酰基；R3 代表含有氮原子和 Z 的环上的官能团；Z 代表形成 5 或 6 元环的二价基团；L 代表 C4-C8 亚烷基或乙烯氧基连接基团，由 (CH2CH2O)nCH2CH2 表示，其中 n 代表 1 或 2；X 代表 O 或 S。
• New Serotonin 5-HT_1A Receptor Agonists with Neuroprotective Effect against Ischemic Cell Damage
  作者：Isabel Marco、Margarita Valhondo、Mar Martı́n-Fontecha、Henar Vázquez-Villa、Joaquı́n Del Rı́o、Anna Planas、Onintza Sagredo、José A. Ramos、Iván R. Torrecillas、Leonardo Pardo、Diana Frechilla、Bellinda Benhamú、Marı́a L. López-Rodrı́guez

  DOI：10.1021/jm2007886

  日期：2011.12.8

  We report the synthesis of new compounds 4 35 based on structural modifications of different moieties of previously described lead UCM-2550. The new nonpiperazine derivatives, representing second-generation agonists, were assessed for binding affinity, selectivity, and functional activity at the 5-HT1A receptor (5-HT1AR). Computational beta(2)-based homology models of the ligand receptor complexes were used to explain the observed structure affinity relationships. Selected candidates were also evaluated for their potential in vitro and in vivo neuroprotective properties. Interestingly, compound 26 (2-6-[(3,4:-dihydro-2H-chromen-2-ylmethyl)amino]hexyl}-tetrahydro-1H-pyrrolo[1,2-c]imidazole-1,3(2H)-dione) has been characterized as a high-affinity and potent 5-HT1AR agonist (K-i, = 5.9 nM, EC50 = 21.8 nM) and exhibits neuroprotective effect in neurotoxicity assays in primary cell cultures from rat hippocampus and in the MCAO model of focal cerebral ischemia in rats.
• US6593323B1
  申请人：——

  公开号：US6593323B1

  公开（公告）日：2003-07-15
• Design, synthesis, and biological evaluation of novel 2,4-thiazolidinedione derivatives as histone deacetylase inhibitors targeting liver cancer cell line
  作者：Rhea Mohan、Ajit K. Sharma、Sanjay Gupta、C. S. Ramaa

  DOI：10.1007/s00044-011-9623-3

  日期：2012.7

  As a part of an ongoing effort to find alternate chemotherapeutic agents for hepatocellular carcinoma, we herein, report the design and synthesis of two novel compounds targeting histone deacetylase (HDAC) with 2,4-thiazolidinedione as zinc chelating group. Further, we demonstrate that these compounds show cytotoxicity that parallels their ability to inhibit HDACs activity in human liver cancer cell line HepG2. The findings obtained in this study indicate that 2,4-thiazolidinedione group may be utilized successfully to inhibit HDAC activity with future potential for lead optimization by chemical derivatization of active compound, N-(6-(2,4-dioxothiazolidin-3- yl)hexyl) benzenesulfonamide.