(1R,2R,15R,18R,19S,22S,27S)-2,14,14,18,19,25,25-heptamethyl-5,12-diazaheptacyclo[16.12.0.02,15.04,13.06,11.019,28.022,27]triaconta-4,6,8,10,12,28-hexaene-22-carboxylic acid | 1084774-90-2

• 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: (1R,2R,15R,18R,19S,22S,27S)-2,14,14,18,19,25,25-heptamethyl-5,12-diazaheptacyclo[16.12.0.02,15.04,13.06,11.019,28.022,27]triaconta-4,6,8,10,12,28-hexaene-22-carboxylic acid
• CAS: 1084774-90-2
• 化学式: C₃₆H₄₈N₂O₂
• 分子量: 540.789
• InChiKey: XEUJIKABFNCODT-KCDITZHISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  40
• 可旋转键数：
  1
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  63.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,2R,15R,18R,19S,22S,27S)-2,14,14,18,19,25,25-heptamethyl-5,12-diazaheptacyclo[16.12.0.02,15.04,13.06,11.019,28.022,27]triaconta-4,6,8,10,12,28-hexaene-22-carboxylic acid 在 草酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  具有抗破骨细胞活性的新型杂环齐墩果酸衍生物的合成与评价

  摘要：

  具有抗骨吸收作用的齐墩果酸是在牛膝的药用植物中发现的活性成分。合成了一系列齐墩果酸的杂环衍生物，包括吲哚，吡嗪，喹喔啉，喹啉部分及其天然氨基酸酰胺。评估了它们对破骨细胞样多核细胞（OCL）形成的抑制活性以及所选衍生物的细胞毒性。在衍生物中，化合物2a和8a即使在200 nM时也显示出相当强的活性。还讨论了衍生物的结构-活性关系。

  DOI：

  10.1016/j.ejmech.2008.12.024
• 作为产物：
  描述：

  2,3-dioxoolean-12-en-28-oic acid 、 邻苯二胺 以 乙醇 为溶剂， 反应 3.0h， 以56%的产率得到(1R,2R,15R,18R,19S,22S,27S)-2,14,14,18,19,25,25-heptamethyl-5,12-diazaheptacyclo[16.12.0.02,15.04,13.06,11.019,28.022,27]triaconta-4,6,8,10,12,28-hexaene-22-carboxylic acid
  参考文献：
  名称：

  Synthesis and biological evaluation of heterocyclic ring-substituted maslinic acid derivatives as novel inhibitors of protein tyrosine phosphatase 1B

  摘要：

  A series of maslinic acid derivatives have been synthesized by introducing various fused heterocyclic rings at C-2 and C-3 positions. Their inhibitory effects on PTP1B, TCPTP and related PTPs are evaluated. Most of the compounds exhibited a dramatic increase in inhibitory potency and selectivity, the two most potent PTP1B inhibitors 20 (IC50 = 0.61 mu M) and 29 (IC50 = 0.64 mu M) showed about 10-fold more potent than lead compound maslinic acid. More importantly, 29 possesses the best selectivity of 6.9-fold for PTP1B over TCPTP. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.10.017

文献信息

• Synthesis and evaluation of a novel series of heterocyclic oleanolic acid derivatives with anti-osteoclast formation activity
  作者：Jun-Feng Li、Yu Zhao、Min-Min Cai、Xiao-Fei Li、Jian-Xin Li

  DOI：10.1016/j.ejmech.2008.12.024

  日期：2009.7

  Oleanolic acid with anti-bone resorption effect was an active component discovered in a medicinal plant of Achyranthes bidentata. A series of heterocyclic derivatives of oleanolic acid including indole, pyrazine, quinoxaline, quinoline moieties and their natural amino acid amides were synthesized. Their inhibitory activity on the formation of osteoclast-like multinucleated cells (OCLs) and cytotoxicity

  具有抗骨吸收作用的齐墩果酸是在牛膝的药用植物中发现的活性成分。合成了一系列齐墩果酸的杂环衍生物，包括吲哚，吡嗪，喹喔啉，喹啉部分及其天然氨基酸酰胺。评估了它们对破骨细胞样多核细胞（OCL）形成的抑制活性以及所选衍生物的细胞毒性。在衍生物中，化合物2a和8a即使在200 nM时也显示出相当强的活性。还讨论了衍生物的结构-活性关系。
• Synthesis and biological evaluation of heterocyclic ring-substituted maslinic acid derivatives as novel inhibitors of protein tyrosine phosphatase 1B
  作者：Wen-Wei Qiu、Qiang Shen、Fan Yang、Bo Wang、Hui Zou、Jing-Ya Li、Jia Li、Jie Tang

  DOI：10.1016/j.bmcl.2009.10.017

  日期：2009.12

  A series of maslinic acid derivatives have been synthesized by introducing various fused heterocyclic rings at C-2 and C-3 positions. Their inhibitory effects on PTP1B, TCPTP and related PTPs are evaluated. Most of the compounds exhibited a dramatic increase in inhibitory potency and selectivity, the two most potent PTP1B inhibitors 20 (IC50 = 0.61 mu M) and 29 (IC50 = 0.64 mu M) showed about 10-fold more potent than lead compound maslinic acid. More importantly, 29 possesses the best selectivity of 6.9-fold for PTP1B over TCPTP. (C) 2009 Elsevier Ltd. All rights reserved.