Methyl-3-oxo-15-norpodocarpa-4,9(11)-dien-8β-carboxylat | 212953-70-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: Methyl-3-oxo-15-norpodocarpa-4,9(11)-dien-8β-carboxylat
• 英文别名: methyl (4aS,8aS)-1,4a-dimethyl-2-oxo-4,6,7,8,9,10-hexahydro-3H-phenanthrene-8a-carboxylate
• CAS: 212953-70-3
• 化学式: C₁₈H₂₄O₃
• 分子量: 288.387
• InChiKey: PYRZWDCBYGRESL-ROUUACIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Methyl-3-oxo-15-norpodocarpa-4,9(11)-dien-8β-carboxylat 在 氨 、 水 、 4-甲基苯磺酸吡啶 、 lithium 作用下， 以 苯 为溶剂， 生成 [(4'aS,8'aS,10'aR)-1',1',4'a-trimethylspiro[1,3-dioxolane-2,2'-3,4,6,7,8,9,10,10a-octahydrophenanthrene]-8'a-yl]methanol
  参考文献：
  名称：

  SYNTHETIC TRITERPENOIDS AND TRICYCLIC-BIS-ENONES FOR USE IN STIMULATING BONE AND CARTILAGE GROWTH

  摘要：

  本发明涉及使用合成三萜类化合物和三环双酮类化合物刺激骨骼和软骨生长和修复的方法。适用的三萜类化合物示例包括CDDO、CDDO-Me、CDDO-Im和CDDO-Ethylamide。适用的三环双酮类化合物示例包括TBE-31和TBE-34。

  公开号：

  US20080233195A1
• 作为产物：
  描述：

  环己酮 在 sodium 、 potassium hydride 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 Methyl-3-oxo-15-norpodocarpa-4,9(11)-dien-8β-carboxylat
  参考文献：
  名称：

  SYNTHETIC TRITERPENOIDS AND TRICYCLIC-BIS-ENONES FOR USE IN STIMULATING BONE AND CARTILAGE GROWTH

  摘要：

  本发明涉及使用合成三萜类化合物和三环双酮类化合物刺激骨骼和软骨生长和修复的方法。适用的三萜类化合物示例包括CDDO、CDDO-Me、CDDO-Im和CDDO-Ethylamide。适用的三环双酮类化合物示例包括TBE-31和TBE-34。

  公开号：

  US20080233195A1

文献信息

• [EN] A NOVEL METHOD FOR SYNTHESIZING TBE-31<br/>[FR] NOUVEAU PROCÉDÉ DE SYNTHÈSE DU TBE-31
  申请人：UNIV NEW YORK STATE RES FOUND

  公开号：WO2014151181A1

  公开（公告）日：2014-09-25

  A process for the synthesis of (±)-(4bS,8aR,10aS)-10a-ethynyl-4b,8,8-trimethyl-3,7-dioxo-3,4b,7,8,8a,9,10,10a-octahydrophenanthrene-2,6-dicarbonitrile ("TBE-31"), which is useful for the treatment of various diseases and disorder in mammals. (±)-8a-(Hydroxymethyl)-1,4a-dimethyl-2,3,4,4a,6,7,8,8a,9,10-decahydrophenanthren-2-ol; (±)-8a-(Hydroxymethyl)-1,4a-dimethyl-4,4a,6,7,8,8a,9,10-octahydrophenanthren-2(3H)-one; (±)-(2R,4aS,8aS)-8a-(Hydroxymethyl)-1,4a-dimethyl-2,3,4,4a,6,7,8,8a,9,10-decahydrophenanthren-2-ol; (±)-(2S,4aS,8aS)-8a-(Hydroxymethyl)-1,4a-dimethyl-2,3,4,4a,6,7,8,8a,9,10-decahydrophenanthren-2-ol; and (±)-(4aS,8aS)-8a-(Hydroxymethyl)-1,4a-dimethyl-4,4a,6,7,8,8a,9,10-octahydrophenanthren-2(3H)-one (4).

  一种合成（±）-（4bS,8aR,10aS）-10a-乙炔基-4b,8,8-三甲基-3,7-二酮-3,4b,7,8,8a,9,10,10a-辛氢苯并-2,6-二腈（“TBE-31”）的方法，该方法对哺乳动物的各种疾病和紊乱具有治疗作用。 （±）-8a-（羟甲基）-1,4a-二甲基-2,3,4,4a,6,7,8,8a,9,10-十氢苯并-2-醇；（±）-8a-（羟甲基）-1,4a-二甲基-4,4a,6,7,8,8a,9,10-辛氢苯并-2（3H）-酮；（±）-（2R,4aS,8aS）-8a-（羟甲基）-1,4a-二甲基-2,3,4,4a,6,7,8,8a,9,10-十氢苯并-2-醇；（±）-（2S,4aS,8aS）-8a-（羟甲基）-1,4a-二甲基-2,3,4,4a,6,7,8,8a,9,10-十氢苯并-2-醇；以及（±）-（4aS,8aS）-8a-（羟甲基）-1,4a-二甲基-4,4a,6,7,8,8a,9,10-辛氢苯并-2（3H）-酮（4）。
• SYNTHESIS AND BIOLOGICAL ACTIVITIES OF NEW TRICYCLIC-BIS-ENONES (TBES)
  申请人：Honda Tadashi

  公开号：US20080261985A1

  公开（公告）日：2008-10-23

  This invention describes novel tricyclic-bis-enone derivatives (TBEs), such as TBE-31, TBE-34, TBE-45 and water-soluble TBEs. The methods of preparing these compounds are also disclosed. The inventors demonstrate the ability of these new TBEs to inhibit proliferation of human myeloma cells, inhibit the induction of iNOS in cells stimulated with interferon-γ, induce heme oxygenase-1 (HO-1), induce CD11b expression—a leukemia differentiation marker, inhibit proliferation of leukemia cells, induce apoptosis in human lung cancer, and induce apoptosis in other cancerous cells. The TBEs of this invention are expected to be useful agents for the treatment and prevention of many diseases, including cancer, neurological disorders, inflammation, and pathologies involving oxidative stress.

  这项发明描述了新的三环双烯酮衍生物（TBEs），如TBE-31、TBE-34、TBE-45和水溶性TBEs。还公开了制备这些化合物的方法。发明人展示了这些新TBEs抑制人骨髓瘤细胞增殖的能力，抑制干扰素-γ刺激下细胞中iNOS的诱导，诱导血红素氧合酶-1（HO-1），诱导CD11b表达-一种白血病分化标志物，抑制白血病细胞增殖，诱导人肺癌细胞凋亡，并诱导其他癌细胞凋亡。这项发明的TBEs预计将成为治疗和预防许多疾病的有用药物，包括癌症、神经系统疾病、炎症和涉及氧化应激的病理学。
• WO2008/64133
  申请人：——

  公开号：——

  公开（公告）日：——
• TRICYCLIC-BIS-ENONE DERIVATIVES AND METHODS OF USE THEREOF
  申请人：Trustees of Dartmouth College

  公开号：EP1465615B1

  公开（公告）日：2012-08-01
• Tricyclic-Bis-Enone Derivatives and Methods of Use Thereof
  申请人：Honda Tadashi

  公开号：US20100261930A1

  公开（公告）日：2010-10-14

  Novel tricyclic-bis-enone derivatives (TBEs) as well as the process for the preparation of such TBEs are provided. Also provided are methods for prevention and/or treatment of cancer, Alzheimer's disease, Parkinson's disease, multiple sclerosis, amyotropic lateral sclerosis, rheumatoid arthritis, inflammatory bowel disease, and all other diseases whose pathogenesis is believed to involve excessive production of either nitric oxide (NO) or prostaglandins or the overexpression of iNOS or COX-2 genes or gene products. Further, methods for the synthesis of the TBE compounds of the invention utilize cheap commercially available reagents and are highly cost effective and amenable to scale-up. Additional high efficiency synthetic methods that utilize novel intermediates as well as the synthesis of these intermediates are also provided. Furthermore, the invention also provides methods for designing novel and water-soluble TBEs.