(E)-12-N-(p-cyanobenzenesulfonyl)-Δ^βγ-sophocarpinic acid | 1399878-43-3

• 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-(p-cyanobenzenesulfonyl)-Δ^βγ-sophocarpinic acid
• 英文别名: (E)-12-N-(p-cyanobenzenesulfonyl)-Δ^αβ-sophocarpinic acid；(E)-4-[(5S,6R,9S,13S)-7-(4-cyanophenyl)sulfonyl-1,7-diazatricyclo[7.3.1.05,13]tridecan-6-yl]but-2-enoic acid
• CAS: 1399878-43-3
• 化学式: C₂₂H₂₇N₃O₄S
• 分子量: 429.54
• InChiKey: XYKZVSBTHLEYQZ-IIDUGZRFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  布雷菲德菌素A 在 potassium carbonate 、 间甲酚 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 21.0h， 生成 (E)-12-N-(p-cyanobenzenesulfonyl)-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

• Synthesis and Biological Evaluation of N‐Substituted Sophocarpinic Acid Derivatives as Coxsackievirus B3 Inhibitors
  作者：Li‐Mei Gao、Sheng Tang、Yan‐Xiang Wang、Rong‐Mei Gao、Xin Zhang、Zong‐Gen Peng、Jian‐Rui Li、Jian‐Dong Jiang、Yu‐Huan Li、Dan‐Qing Song

  DOI：10.1002/cmdc.201300224

  日期：2013.9

  A series of novel N‐substituted sophocarpinic acid derivatives was designed, synthesized, and evaluated for their anti‐enteroviral activities against coxsackievirus type B3 (CVB3) and coxsackievirus type B6 (CVB6) in Vero cells. Structure–activity relationship analysis revealed that the introduction of a benzenesulfonyl moiety on the 12‐nitrogen atom in (E)‐β,γ‐sophocarpinic acid might significantly

  设计，合成和评估了一系列新颖的N取代的果几磷酸衍生物对Vero细胞中针对B3型柯萨奇病毒（CVB3）和B6型柯萨奇病毒（CVB6）的抗肠病毒活性。结构-活性关系分析表明，在（E）-β，γ-次果酸中的12-氮原子上引入苯磺酰基部分可能会显着增强抗CVB3活性。间的衍生物，（É）-12- ñ - （米-cyanobenzenesulfonyl）-β，γ-sophocarpinic酸（11米），具有一元-cyanobenzenesulfonyl基，表现出对CVB3有效的活性与107的选择性指数（SI） 。此外，化合物11 m也表现出良好的口腔药代动力学分布，具有7.29的AUC值μ中号 ħ -1大鼠，和良好的安全性，通过在小鼠中口服途径，与LD 50 > 1000毫克公斤的值-1 ; 这些值表明有可药物治疗的特征。因此，化合物11 m被选作有希望的CVB3抑制剂作进一步研究。我们认为（E）-β，γ-
• 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.