2-cyano-1-en-3-one betulinic acid | 918937-57-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2-cyano-1-en-3-one betulinic acid
• 英文别名: 2-cyano-3-oxolupa-1,20(29)-dien-28-oic acid；ALS 862；(1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-10-cyano-5a,5b,8,8,11a-pentamethyl-9-oxo-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,9,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysene-3a-carboxylic acid；(1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-10-cyano-5a,5b,8,8,11a-pentamethyl-9-oxo-1-prop-1-en-2-yl-2,3,4,5,6,7,7a,11b,12,13,13a,13b-dodecahydro-1H-cyclopenta[a]chrysene-3a-carboxylic acid
• CAS: 918937-57-2
• 化学式: C₃₁H₄₃NO₃
• 分子量: 477.687
• InChiKey: WXZMJXNGGUJSIL-AJNNAGPSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  35
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  78.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-cyano-1-en-3-one betulinic acid 在 草酰氯 作用下， 以 二氯甲烷 为溶剂， 以100%的产率得到(1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-10-Cyano-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-9-oxo-1,2,3,4,5,5a,5b,6,7,7a,8,9,11a,11b,12,13,13a,13b-octadecahydro-cyclopenta[a]chrysene-3a-carbonyl chloride
  参考文献：
  名称：

  Design, synthesis, and anti-inflammatory activity both in vitro and in vivo of new betulinic acid analogues having an enone functionality in ring A

  摘要：

  Fifteen new betulinic acid analogues were designed, synthesized, and tested for anti-inflammatory activity. Many of these analogues effectively suppress nitric oxide (NO) production in RAW cells stimulated with interferon-gamma. Analogue 10 is highly and orally active in vivo for induction of the anti-inflammatory and cytoprotective enzyme, heme oxygenase-1. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.09.012
• 作为产物：
  描述：

  ALS-769 在 Jones reagent 作用下， 以 丙酮 为溶剂， 反应 4.0h， 以57%的产率得到2-cyano-1-en-3-one betulinic acid
  参考文献：
  名称：

  Synthetic pentacyclic triterpenoids and derivatives of betulinic acid and betulin

  摘要：

  本发明包括细胞增殖状况的小分子抑制剂，特别是癌症及与癌症相关的状况。例如，相关的恶性肿瘤包括卵巢癌、宫颈癌、乳腺癌、结直肠癌和胶质母细胞瘤等。因此，本发明的化合物对于治疗、预防和/或抑制这些疾病是有用的。因此，本发明还包括包含这些化合物的药物配方以及使用这些化合物和配方来抑制癌症并治疗、预防或抑制上述疾病的方法。

  公开号：

  US20070232577A1

文献信息

• Synthetic pentacyclic triterpenoids and derivatives of betulinic acid and betulin
  申请人：Xu Ze-Qi

  公开号：US20070232577A1

  公开（公告）日：2007-10-04

  The present invention comprises small molecule inhibitors of cell proliferative conditions, in particular cancer and conditions associated with cancer. For example, associated malignancies include ovarian cancer, cervical cancer, breast cancer, colorectal cancer, and glioblastomas, among others. Accordingly, the compounds of the present invention are useful for treating, preventing, and/or inhibiting these diseases. Thus, the present invention also comprising pharmaceutical formulations comprising the compounds and methods of using the compounds and formulations to inhibit cancer and treat, prevent, or inhibit the foregoing diseases.

  本发明包括细胞增殖状况的小分子抑制剂，特别是癌症及与癌症相关的状况。例如，相关的恶性肿瘤包括卵巢癌、宫颈癌、乳腺癌、结直肠癌和胶质母细胞瘤等。因此，本发明的化合物对于治疗、预防和/或抑制这些疾病是有用的。因此，本发明还包括包含这些化合物的药物配方以及使用这些化合物和配方来抑制癌症并治疗、预防或抑制上述疾病的方法。
• 2-Cyano-3,10-dioxooleana-1,9(11)-dien-28-oic acid anhydride. A novel and highly potent anti-inflammatory and cytoprotective agent
  作者：Tadashi Honda、Eric M. Padegimas、Emilie David、Chitra Sundararajan、Karen T. Liby、Charlotte Williams、Michael B. Sporn、Melean Visnick

  DOI：10.1016/j.bmcl.2010.02.007

  日期：2010.4

  2-Cyano-3,10-dioxooleana-1,9(11)-dien-28-oic acid anhydride (CDDO anhydride) has been synthesized, which is the first example of an oleanane triterpenoid anhydride. CDDO anhydride shows potency similar to or higher than the corresponding acid (CDDO) in various in vitro and in vivo assays related to inflammation and carcinogenesis. Notably, preliminary phamacokinetics studies show that CDDO anhydride levels are higher than CDDO levels in mouse tissues and blood. Further evaluation of CDDO anhydride is in progress. (C) 2010 Elsevier Ltd. All rights reserved.
• [EN] SYNTHETIC PENTACYCLIC TRITERPENOIDS AND DERIVATIVES OF BETULINIC ACID AND BETULIN<br/>[FR] TRITERPENOIDES PENTACYCLIQUES SYNTHETIQUES ET DERIVES D'ACIDE BETULINIQUE ET DE BETULINE
  申请人：ADVANCED LIFE SCIENCES INC

  公开号：WO2007112043A2

  公开（公告）日：2007-10-04

  [EN] The present invention comprises small molecule inhibitors of cell proliferative conditions, in particular cancer and conditions associated with cancer. For example, associated malignancies include ovarian cancer, cervical cancer, breast cancer, colorectal cancer, and glioblastomas, among others. Accordingly, the compounds of the present invention are useful for treating, preventing, and/or inhibiting these diseases. Thus, the present invention also comprising pharmaceutical formulations comprising the compounds and methods of using the compounds and formulations to inhibit cancer and treat, prevent, or inhibit the foregoing diseases.
  [FR] La présente invention concerne des inhibiteurs à petite molécule d'affections de la prolifération cellulaire, en particulier du cancer et des affections associées au cancer. Par exemple, les malignités associées incluent le cancer de l'ovaire, le cancer du col de l'utérus, le cancer du sein, le cancer colorectal et les glioblastomes, entre autres. Les composés de la présente invention sont par conséquent utiles pour le traitement, la prévention et/ou l'inhibition de ces maladies. Ainsi, la présente invention concerne également des formulations pharmaceutiques comprenant ces composés, et les procédés d'utilisation des composés et des formulations afin d'inhiber le cancer et traiter, prévenir, ou inhiber les maladies susmentionnées.
• Design, synthesis, and anti-inflammatory activity both in vitro and in vivo of new betulinic acid analogues having an enone functionality in ring A
  作者：Tadashi Honda、Karen T. Liby、Xiaobo Su、Chitra Sundararajan、Yukiko Honda、Nanjoo Suh、Renee Risingsong、Charlotte R. Williams、Darlene B. Royce、Michael B. Sporn、Gordon W. Gribble

  DOI：10.1016/j.bmcl.2006.09.012

  日期：2006.12

  Fifteen new betulinic acid analogues were designed, synthesized, and tested for anti-inflammatory activity. Many of these analogues effectively suppress nitric oxide (NO) production in RAW cells stimulated with interferon-gamma. Analogue 10 is highly and orally active in vivo for induction of the anti-inflammatory and cytoprotective enzyme, heme oxygenase-1. (c) 2006 Elsevier Ltd. All rights reserved.
• Synthesis and cytotoxicity of 2-cyano-28-hydroxy-lup-1-en-3-ones
  作者：Ali Koohang、Nathan D. Majewski、Erika L. Szotek、Aye Aye Mar、David A. Eiznhamer、Michael T. Flavin、Ze-Qi Xu

  DOI：10.1016/j.bmcl.2009.02.107

  日期：2009.4

  New A-ring modified betulin and dihydrobetulin derivatives possessing the 2-cyano-1-en-3-one moiety were prepared and tested for cytotoxicity in seven cancer cell lines. The most active agent 9a synthesized in this account was further demonstrated to induce apoptosis and to activate caspases in malignant melanoma cells. (C) 2009 Elsevier Ltd. All rights reserved.