2-(chloroselenyl)-5-methylbenzoyl chloride | 494769-32-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(chloroselenyl)-5-methylbenzoyl chloride
• 英文别名: 5-methyl-2-selenochlorobenzoyl chloride；5-methyl-2-(chloroseleno)benzoyl chloride；(2-Carbonochloridoyl-4-methylphenyl) selenohypochlorite
• CAS: 494769-32-3
• 化学式: C₈H₆Cl₂OSe
• 分子量: 268.001
• InChiKey: FUJNTOVCLKNKGT-UHFFFAOYSA-N

物化性质

• 沸点：
  354.4±35.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.86
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,6-己二胺 、 2-(chloroselenyl)-5-methylbenzoyl chloride 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以82%的产率得到5-Methyl-2-[6-(5-methyl-3-oxo-1,2-benzoselenazol-2-yl)hexyl]-1,2-benzoselenazol-3-one
  参考文献：
  名称：

  Inhibition of thioredoxin reductase by a novel series of bis-1,2-benzisoselenazol-3(2H)-ones: Organoselenium compounds for cancer therapy

  摘要：

  Thioredoxin reductase (TrxR) is critical for cellular redox regulation and is involved in tumor proliferation, apoptosis and metastasis. Its C-terminal redox-active center contains a cysteine (Cys497) and a unique selenocysteine (Sec498), which are exposed to solvent and easily accessible. Thus, it is becoming an important target for anticancer drugs. Selective inhibition of TrxR by 1,2-(bis-1,2-benzisoselenazol-3(2H)-one)ethane (4a) prevents proliferation of several cancer cell lines both in vivo and in vitro. Using the structure of 4a as a starting point, a series of novel bis-1,2-benzisoselenazol-3(2H)-ones was designed, prepared and tested to explore the structure-activity relationships (SARs) for this class of inhibitor and to improve their potency. Notably, 1,2-(5,5'-dimethoxybis(1,2-benzisoselenazol-3(2H)-one))ethane (12) was found to be more potent than 4a in both in vitro and in vivo evaluation. Its binding sites were confirmed by biotin-conjugated iodoacetamide assay and a SAR model was generated to guide further structural modification. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.04.033
• 作为产物：
  描述：

  2-氨基-5-甲基苯甲酸 在 盐酸 、 氯化亚砜 、 disodium diselenide 、 sodium nitrite 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 2-(chloroselenyl)-5-methylbenzoyl chloride
  参考文献：
  名称：

  苯并异硒唑酮类化合物代谢物、其合成方法及 其应用

  摘要：

  本发明提供一种具有通式(Ⅰ)的苯并异硒唑衍生物或其药物学上可接受的盐：其中：R1、R2相同或不同，各自独立为氢、卤素(例如F、Cl)、腈基、硝基、C1‑C6烷基、C1‑C6烷氧基、C1‑C6烷硫基、N(C1‑C6烷基)2、NH(C1‑C6烷基)、COOH、SO3H。本发明还提供包含该化合物的药用组合物及其在制备抗肿瘤药物中的应用。

  公开号：

  CN106146371B

文献信息

• Synthesis and antiproliferative evaluation of novel steroid-benzisoselenazolone hybrids
  作者：Jianguo Cui、Meizhen Wei、Liping Pang、Chunfang Gan、Junan Xiao、Haixin Shi、Junyan Zhan、Zhiping Liu、Yanmin Huang

  DOI：10.1016/j.steroids.2019.108502

  日期：2019.12

  The two different types of steroidal benzisoselenazolone hybrids were synthesized by incorporating benzisoselenazolone scaffold into dehydroepiandrosterone and B-norcholesterol. The antiproliferative activity of the synthesized compounds against some carcinoma cell lines were investigated. The results showed that some of these compounds have better inhibitory activity than abiraterone on the proliferation of tumor cells associated with human growth hormone, and have less cytotoxicity on normal human cells. In particular, the IC50 values of the compound 8a and 8f are 5.4 and 6.5 mu mol/L against human ovarian carcinoma (SKOV3) cell line, and possess SI values of 13.9 and 10.5, respectively. The information obtained from the studies may be useful for the design of novel chemotherapeutic drugs.
• EP4112608
  申请人：——

  公开号：——

  公开（公告）日：——
• Inhibition of thioredoxin reductase by a novel series of bis-1,2-benzisoselenazol-3(2H)-ones: Organoselenium compounds for cancer therapy
  作者：Jie He、Dongdong Li、Kun Xiong、Yongjie Ge、Hongwei Jin、Guozhou Zhang、Mengshi Hong、Yongliang Tian、Jin Yin、Huihui Zeng

  DOI：10.1016/j.bmc.2012.04.033

  日期：2012.6

  Thioredoxin reductase (TrxR) is critical for cellular redox regulation and is involved in tumor proliferation, apoptosis and metastasis. Its C-terminal redox-active center contains a cysteine (Cys497) and a unique selenocysteine (Sec498), which are exposed to solvent and easily accessible. Thus, it is becoming an important target for anticancer drugs. Selective inhibition of TrxR by 1,2-(bis-1,2-benzisoselenazol-3(2H)-one)ethane (4a) prevents proliferation of several cancer cell lines both in vivo and in vitro. Using the structure of 4a as a starting point, a series of novel bis-1,2-benzisoselenazol-3(2H)-ones was designed, prepared and tested to explore the structure-activity relationships (SARs) for this class of inhibitor and to improve their potency. Notably, 1,2-(5,5'-dimethoxybis(1,2-benzisoselenazol-3(2H)-one))ethane (12) was found to be more potent than 4a in both in vitro and in vivo evaluation. Its binding sites were confirmed by biotin-conjugated iodoacetamide assay and a SAR model was generated to guide further structural modification. (C) 2012 Elsevier Ltd. All rights reserved.
• 苯并异硒唑酮类化合物代谢物、其合成方法及 其应用
  申请人：南京凯熙医学科技有限公司

  公开号：CN106146371B

  公开（公告）日：2018-05-15

  本发明提供一种具有通式(Ⅰ)的苯并异硒唑衍生物或其药物学上可接受的盐：其中：R1、R2相同或不同，各自独立为氢、卤素(例如F、Cl)、腈基、硝基、C1‑C6烷基、C1‑C6烷氧基、C1‑C6烷硫基、N(C1‑C6烷基)2、NH(C1‑C6烷基)、COOH、SO3H。本发明还提供包含该化合物的药用组合物及其在制备抗肿瘤药物中的应用。