kurarinol | 1332258-87-3

• 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: kurarinol
• 英文别名: matrinol；DM-200；4-[(5R,6R,9S,13S)-1,7-diazatricyclo[7.3.1.05,13]tridecan-6-yl]butan-1-ol
• CAS: 1332258-87-3
• 化学式: C₁₅H₂₈N₂O
• 分子量: 252.4
• InChiKey: WFLQENPHTVNLGT-YJNKXOJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  35.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  kurarinol 在 咪唑 、 盐酸 、 三乙胺 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 12-N-(m-cyanobenzenesulfonyl)matrinol 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：

  苦参碱 在 lithium aluminium tetrahydride 、 水 、 potassium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 kurarinol
  参考文献：
  名称：

  Synthesis, structure−activity relationship and biological evaluation of novel N-substituted matrinic acid derivatives as host heat-stress cognate 70 (Hsc70) down-regulators

  摘要：

  Oxymatrine (1) is a natural anti-hepatitis B virus (HBV) drug that down-regulates host heat-stress cognate 70 (Hsc70) expression through a mechanism different from that of nucleosides. Taking Hsc70 as a target against HBV, 26 novel N-substituted matrinic acid analogs were designed, synthesized and evaluated for their regulation of Hsc70 mRNA expression with 1 as the lead. The SAR analysis revealed that (i) the carboxyl group at the 11-position was required for activity; (ii) introducing of a substituent on the nitrogen atom at the 12-position of 3, especially substituted benzyl, might significantly improve the activity. Among these analogs, compound 9p possessing N-p-methoxylbenzyl afforded an increased anti-HBV effect in comparison with 1. We consider 9p a promising anti-HBV candidate. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.071

文献信息

• EP2581376
  申请人：——

  公开号：——

  公开（公告）日：——
• 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.
• Synthesis, structure−activity relationship and biological evaluation of novel N-substituted matrinic acid derivatives as host heat-stress cognate 70 (Hsc70) down-regulators
  作者：Na-Na Du、Xin Li、Yu-Ping Wang、Fei Liu、Yan-Xin Liu、Chun-Xin Li、Zong-Gen Peng、Li-Mei Gao、Jian-Dong Jiang、Dan-Qing Song

  DOI：10.1016/j.bmcl.2011.06.071

  日期：2011.8

  Oxymatrine (1) is a natural anti-hepatitis B virus (HBV) drug that down-regulates host heat-stress cognate 70 (Hsc70) expression through a mechanism different from that of nucleosides. Taking Hsc70 as a target against HBV, 26 novel N-substituted matrinic acid analogs were designed, synthesized and evaluated for their regulation of Hsc70 mRNA expression with 1 as the lead. The SAR analysis revealed that (i) the carboxyl group at the 11-position was required for activity; (ii) introducing of a substituent on the nitrogen atom at the 12-position of 3, especially substituted benzyl, might significantly improve the activity. Among these analogs, compound 9p possessing N-p-methoxylbenzyl afforded an increased anti-HBV effect in comparison with 1. We consider 9p a promising anti-HBV candidate. (C) 2011 Elsevier Ltd. All rights reserved.