(E)-12-N-(o-trifluoromethybenzenesulfonyl)-Δ^βγ-sophocarpinic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: (E)-12-N-(o-trifluoromethybenzenesulfonyl)-Δ^βγ-sophocarpinic acid
• 英文别名: (E)-4-[(5S,6R,9S,13S)-7-[2-(trifluoromethyl)phenyl]sulfonyl-1,7-diazatricyclo[7.3.1.05,13]tridecan-6-yl]but-3-enoic acid
• 化学式: C₂₂H₂₇F₃N₂O₄S
• 分子量: 472.529
• InChiKey: UORKWVOEXXWSOY-OSLMROANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  86.3
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  甲醇 、 (E)-12-N-(o-trifluoromethybenzenesulfonyl)-Δ^βγ-sophocarpinic acid 在 盐酸 作用下， 反应 2.0h， 以420 mg的产率得到methyl (E)-12-N-(o-trifluoromethybenzenesulfonyl)-Δ^βγ-sophocarpinate hydrochloride
  参考文献：
  名称：

  Novel N-Benzenesulfonyl Sophocarpinol Derivatives as Coxsackie B Virus Inhibitors

  摘要：

  Novel N-benzenesulfonyl sophocarpinic acid/ester and sophocarpinol derivatives were synthesized and evaluated for their antienteroviral activities against coxsackievirus type B3 (CVB3) from sophocarpine (1), a natural medicine isolated from Chinese herb. Structure-activity relationship (SAR) analysis revealed that the double bond and its geometrical configuration and position at the C-11 attachment did not greatly affect the potency. Among these derivatives, sophocarpinol 24d exerted the promising activities against not only CVB3 but also CVB1, CVB2, CVB5, and CVB6 with IC50 ranging from 0.62 to 3.63 μM (SI from 46 to 275), indicating a broad-spectrum antienteroviral characteristic. The SAR results provided the powerful information for further strategic optimization and development of a novel scaffold of broad-spectrum antiviral candidates against enteroviruses.

  DOI：

  10.1021/ml500525s
• 作为产物：
  描述：

  2-三氟甲基苯磺酰氯 在 间甲酚 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 21.0h， 生成 (E)-12-N-(o-trifluoromethybenzenesulfonyl)-Δ^βγ-sophocarpinic acid
  参考文献：
  名称：

  Novel N-Benzenesulfonyl Sophocarpinol Derivatives as Coxsackie B Virus Inhibitors

  摘要：

  Novel N-benzenesulfonyl sophocarpinic acid/ester and sophocarpinol derivatives were synthesized and evaluated for their antienteroviral activities against coxsackievirus type B3 (CVB3) from sophocarpine (1), a natural medicine isolated from Chinese herb. Structure-activity relationship (SAR) analysis revealed that the double bond and its geometrical configuration and position at the C-11 attachment did not greatly affect the potency. Among these derivatives, sophocarpinol 24d exerted the promising activities against not only CVB3 but also CVB1, CVB2, CVB5, and CVB6 with IC50 ranging from 0.62 to 3.63 μM (SI from 46 to 275), indicating a broad-spectrum antienteroviral characteristic. The SAR results provided the powerful information for further strategic optimization and development of a novel scaffold of broad-spectrum antiviral candidates against enteroviruses.

  DOI：

  10.1021/ml500525s

文献信息

• Novel <i>N</i>-Benzenesulfonyl Sophocarpinol Derivatives as Coxsackie B Virus Inhibitors
  作者：Sheng Tang、Lanying Kong、Yinghong Li、Jiandong Jiang、Limei Gao、Xinyue Cheng、Linlin Ma、Xin Zhang、Yuhuan Li、Danqing Song

  DOI：10.1021/ml500525s

  日期：2015.2.12

  Novel N-benzenesulfonyl sophocarpinic acid/ester and sophocarpinol derivatives were synthesized and evaluated for their antienteroviral activities against coxsackievirus type B3 (CVB3) from sophocarpine (1), a natural medicine isolated from Chinese herb. Structure-activity relationship (SAR) analysis revealed that the double bond and its geometrical configuration and position at the C-11 attachment did not greatly affect the potency. Among these derivatives, sophocarpinol 24d exerted the promising activities against not only CVB3 but also CVB1, CVB2, CVB5, and CVB6 with IC50 ranging from 0.62 to 3.63 μM (SI from 46 to 275), indicating a broad-spectrum antienteroviral characteristic. The SAR results provided the powerful information for further strategic optimization and development of a novel scaffold of broad-spectrum antiviral candidates against enteroviruses.