齐墩果-2,12-二烯[2,3-d]异恶唑-28-酸 | 218600-48-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 齐墩果-2,12-二烯[2,3-d]异恶唑-28-酸
• 英文名称: isoxazolo[4,5-b]olean-12-en-28-oic acid
• 英文别名: Oleana-2,12-dieno[2,3-d]isoxazol-28-oic acid；(1R,2S,5S,10S,14R,15R,23R)-1,2,8,8,15,22,22-heptamethyl-20-oxa-19-azahexacyclo[12.11.0.02,11.05,10.015,23.017,21]pentacosa-11,17(21),18-triene-5-carboxylic acid
• CAS: 218600-48-7
• 化学式: C₃₁H₄₅NO₃
• 分子量: 479.703
• InChiKey: KAVKWHJDPYCYQA-VNNAKPRGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  35
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  63.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  齐墩果-2,12-二烯[2,3-d]异恶唑-28-酸 在 sodium methylate 作用下， 以 甲醇 、 乙醚 为溶剂， 以98%的产率得到(4aS,6aS,6bR,12aR)-11-cyano-2,2,6a,6b,9,9,12a-heptamethyl-10-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid
  参考文献：
  名称：

  Therapeutic compounds and methods of use

  摘要：

  化合物和方法可用于化学预防治疗诸如癌症、阿尔茨海默病、帕金森病、炎症性肠病和多发性硬化等疾病。

  公开号：

  US09278913B2
• 作为产物：
  描述：

  齐墩果-2,12-二烯[2,3-d]异恶唑-28-酸苯甲酯 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 2.0h， 以12%的产率得到齐墩果-2,12-二烯[2,3-d]异恶唑-28-酸
  参考文献：
  名称：

  五环三萜。第3部分：齐墩果酸衍生物作为糖原磷酸化酶的新型抑制剂的合成和生物学评估。

  摘要：

  齐墩果酸及其合成衍生物已被鉴定为糖原磷酸化酶的新型抑制剂。在这一系列化合物中，4（IC50 = 3.3 microM）是最有效的GPa抑制剂。讨论了齐墩果酸衍生物的初步结构-活性关系。

  DOI：

  10.1016/j.bmcl.2006.03.009

文献信息

• Novel heterocyclic ring-fused oleanolic acid derivatives as osteoclast inhibitors for osteoporosis
  作者：Jing Wu、Bei-Hua Bao、Qi Shen、Yu-Chao Zhang、Qing Jiang、Jian-Xin Li

  DOI：10.1039/c5md00482a

  日期：——

  A series of novel oleanolic acid (OA) derivatives were synthesized via modifications of the A-ring and C28-amides of OA, and their anti-bone resorption activities were evaluated in vitro and in vivo.

  一系列新颖的齐墩酸（OA）衍生物通过对OA的A环和C28酰胺进行改造合成，并评估它们的抗骨吸收活性体外和体内。
• Design and synthesis of 2-cyano-3,12-dioxoolean-1,9-dien-28-oic acid, a novel and highly active inhibitor of nitric oxide production in mouse macrophages
  作者：Tadashi Honda、BarbieAnn V. Rounds、Gordon W. Gribble、Nanjoo Suh、Yongping Wang、Michael B. Sporn

  DOI：10.1016/s0960-894x(98)00479-x

  日期：1998.10

  New derivatives with electron-withdrawing substituents at the C-2 position of 3-oxoolean-1-en-28-oic acid were synthesized. Among them, 2-cyano-3,12-dioxoolean-1,9-dien-28-oic acid (CDDO) was 400 times more potent than previous compounds we have made as an inhibitor of production of nitric oxide induced by interferon-gamma in mouse macrophages (IC50, 0.4 nM). The potency of CDDO was similar to that of dexamethasone, although CDDO does not act through the glucocorticoid receptor. (C) 1998 Elsevier Science Ltd. All rights reserved.
• 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.
• THERAPEUTIC COMPOUNDS AND METHODS OF USE
  申请人：Gribble Gordon W.

  公开号：US20130237721A1

  公开（公告）日：2013-09-12

  Compounds and methods useful for chemopreventative treatment of diseases such as cancer, Alzheimer's disease, Parkinson's disease, inflammatory bowel diseases, and multiple sclerosis.
• US20140275618A1
  申请人：——

  公开号：US20140275618A1

  公开（公告）日：2014-09-18