2-[(5-amino-1,3,4-thiadiazol-2-yl)sulfanyl]-N-(5-bromopyridin-2-yl)acetamide | 312285-72-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-[(5-amino-1,3,4-thiadiazol-2-yl)sulfanyl]-N-(5-bromopyridin-2-yl)acetamide
• CAS: 312285-72-6
• 化学式: C₉H₈BrN₅OS₂
• mdl: MFCD01305396
• 分子量: 346.231
• InChiKey: XNADGUDNLYDRHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  147
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-[(5-amino-1,3,4-thiadiazol-2-yl)sulfanyl]-N-(5-bromopyridin-2-yl)acetamide 、 2,6-二氯苯甲酰氯 在 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 4.08h， 以76%的产率得到N-[5-[2-[(5-bromopyridin-2-yl)amino]-2-oxoethyl]sulfanyl-1,3,4-thiadiazol-2-yl]-2,6-dichlorobenzamide
  参考文献：
  名称：

  Novel small molecules as apoptosis inducers: Synthesis, preliminary structure–activity relationships, and in vitro biological evaluation

  摘要：

  Inducing apoptosis is a promising therapeutic approach to overcome cancer. In this study, 30 compounds were synthesized and evaluated for their antiproliferative activity against three tumor cell lines in vitro: A875, H460 and Hela cancer cells by the MTT assay. The most potent analogue 7a, a novel compound was first reported by our group, inhibited the proliferation of A875 cells with an IC50 value of 98 nM. Flow cytometry analysis and morphological analysis suggested that compound 7a had potential anticancer efficacy via G(2)/M cell cycle arrest, which could be attributed to its proliferation and apoptosis, and also in a concentration-dependent manner. The SAR analysis indicated that the substituents R-2 played a crucial role in the antiproliferation activity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.02.076
• 作为产物：
  描述：

  2-氨基-5-溴吡啶 在 potassium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 9.08h， 生成 2-[(5-amino-1,3,4-thiadiazol-2-yl)sulfanyl]-N-(5-bromopyridin-2-yl)acetamide
  参考文献：
  名称：

  Novel small molecules as apoptosis inducers: Synthesis, preliminary structure–activity relationships, and in vitro biological evaluation

  摘要：

  Inducing apoptosis is a promising therapeutic approach to overcome cancer. In this study, 30 compounds were synthesized and evaluated for their antiproliferative activity against three tumor cell lines in vitro: A875, H460 and Hela cancer cells by the MTT assay. The most potent analogue 7a, a novel compound was first reported by our group, inhibited the proliferation of A875 cells with an IC50 value of 98 nM. Flow cytometry analysis and morphological analysis suggested that compound 7a had potential anticancer efficacy via G(2)/M cell cycle arrest, which could be attributed to its proliferation and apoptosis, and also in a concentration-dependent manner. The SAR analysis indicated that the substituents R-2 played a crucial role in the antiproliferation activity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.02.076