2-溴-N-[(4-氯苯基)磺酰基]乙酰胺 | 1048660-67-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-溴-N-[(4-氯苯基)磺酰基]乙酰胺
• 英文名称: 2-bromo-N-((4-chlorophenyl)sulfonyl)acetamide
• 英文别名: 2-bromo-N-(4-chlorophenyl)sulfonylacetamide
• CAS: 1048660-67-8
• 化学式: C₈H₇BrClNO₃S
• 分子量: 312.571
• InChiKey: WTNJLRPPMLVXJM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  71.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-溴-N-[(4-氯苯基)磺酰基]乙酰胺 、 尿素 以 乙醇 为溶剂， 反应 4.0h， 以62%的产率得到N-(2-aminooxazol-4-yl)-4-chlorobenzenesulfonamide
  参考文献：
  名称：

  Synthesis, antimicrobial activity and quantum calculations of Novel sulphonamide derivatives

  摘要：

  THE reactivity of 2-bromo-N-(phenylsulfonyl) acetamide derivatives 3a-c towards some nitrogen-based nucleophiles was studied in this investigation and gave the corresponding aminothiazole 6a-c, aminooxazole 7a-c, quinazoline-2-yl 10a-c; respectively. Furthermore, the reaction of acetamide derivatives 3a-c with aminopyridine gave pyridine-4-ylamino 12a-c. Reaction of acetamide derivatives 3a-c with benzo-2-thiol derivatives afforded benzo [d]thiazol-2-ylthio 14a-c and 1H-benzo[d]imidazol-2-yl) thio derivatives 16a-c; respectively. The synthesized compounds displayed good antimicrobial activity. Additionally, compounds 12a and 14a exhibited high activity towards most of the strains. The computational calculations for 12a and 14a were carried out via HF/6-31G(d) and DFT B3LYP/6-31G(d) basis sets and the corresponding results of HOMO-LUMO energy gap and Mulliken atomic charges were tabulated. This correlation between experimental and theoretical calculations provided a good confirmation for anticipated new compounds.

  DOI：

  10.21608/ejchem.2019.6870.1575
• 作为产物：
  描述：

  4-氯苯磺酰胺 、 溴乙酰溴 以 甲苯 为溶剂， 反应 5.0h， 生成 2-溴-N-[(4-氯苯基)磺酰基]乙酰胺
  参考文献：
  名称：

  Highly Specific and Broadly Potent Inhibitors of Mammalian Secreted Phospholipases A₂

  摘要：

  We report a series of inhibitors of secreted phospholipases A(2) (sPLA(2)S) based on substituted indoles, 6,7-benzoindoles, and indolizines derived from LY315920, a well-known indole-based sPLA(2) inhibitor. Using the human group X sPLA2 crystal structure, we prepared a highly potent and selective indole-based inhibitor of this enzyme. Also, we report human and mouse group IIA and HE specific inhibitors and a substituted 6,7-benzoindole that inhibits nearly all human and mouse sPLAs in the low nanomolar range.

  DOI：

  10.1021/jm800422v

文献信息

• Highly Specific and Broadly Potent Inhibitors of Mammalian Secreted Phospholipases A₂
  作者：Rob C. Oslund、Nathan Cermak、Michael H. Gelb

  DOI：10.1021/jm800422v

  日期：2008.8.1

  We report a series of inhibitors of secreted phospholipases A(2) (sPLA(2)S) based on substituted indoles, 6,7-benzoindoles, and indolizines derived from LY315920, a well-known indole-based sPLA(2) inhibitor. Using the human group X sPLA2 crystal structure, we prepared a highly potent and selective indole-based inhibitor of this enzyme. Also, we report human and mouse group IIA and HE specific inhibitors and a substituted 6,7-benzoindole that inhibits nearly all human and mouse sPLAs in the low nanomolar range.
• Synthesis, antimicrobial activity and quantum calculations of Novel sulphonamide derivatives
  作者：Asmaa Fahim、Eman Ismael

  DOI：10.21608/ejchem.2019.6870.1575

  日期：2019.2.19

  THE reactivity of 2-bromo-N-(phenylsulfonyl) acetamide derivatives 3a-c towards some nitrogen-based nucleophiles was studied in this investigation and gave the corresponding aminothiazole 6a-c, aminooxazole 7a-c, quinazoline-2-yl 10a-c; respectively. Furthermore, the reaction of acetamide derivatives 3a-c with aminopyridine gave pyridine-4-ylamino 12a-c. Reaction of acetamide derivatives 3a-c with benzo-2-thiol derivatives afforded benzo [d]thiazol-2-ylthio 14a-c and 1H-benzo[d]imidazol-2-yl) thio derivatives 16a-c; respectively. The synthesized compounds displayed good antimicrobial activity. Additionally, compounds 12a and 14a exhibited high activity towards most of the strains. The computational calculations for 12a and 14a were carried out via HF/6-31G(d) and DFT B3LYP/6-31G(d) basis sets and the corresponding results of HOMO-LUMO energy gap and Mulliken atomic charges were tabulated. This correlation between experimental and theoretical calculations provided a good confirmation for anticipated new compounds.