3β-methoxylup-20(29)-en-28-oic acid | 173106-55-3

• 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: 3β-methoxylup-20(29)-en-28-oic acid
• 英文别名: 3-O-methylbetulinic acid；3β-methoxybetulinic acid；3β-3-methoxylup-20(29)-en-28-oic acid；3-Methoxylupan-28-oic Acid；(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-methoxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid
• CAS: 173106-55-3
• 化学式: C₃₁H₅₀O₃
• 分子量: 470.736
• InChiKey: CUILEYPJZZWNHU-JVRMVBBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  34
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3β-methoxylup-20(29)-en-28-oic acid 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 methyl 11-[[(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-methoxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carbonyl]amino]undecanoate
  参考文献：
  名称：

  Betulinic Acid Derivatives:  A New Class of Human Immunodeficiency Virus Type 1 Specific Inhibitors with a New Mode of Action

  摘要：

  A series of omega-undecanoic amides of lup-20(29)-en-28-oic acid derivatives were synthesized and evaluated for activity in CEM 4 and MT-4 cell cultures against human immunodeficiency virus type 1 (HIV-1) strain IIIB/LAI. The potent HIV inhibitors which emerged, compounds 5a, 16a, and 17b, were all derivatives of betulinic acid (3 beta-hydroxylup-20(29)-en-28-oic acid). No activity was found against HIV-2 strain ROD. Compound 5a showed no inhibition of HIV-1 reverse transcriptase activity with poly(C). oligo(dG) as template/primer, nor did it inhibit HIV-1 protease. Additional mechanistic studies revealed that this class of compounds interfere with HIV-1 entry in the cells at a postbinding step.

  DOI：

  10.1021/jm950670t
• 作为产物：
  描述：

  methyl 3β-methoxylup-20(29)-en-28-oate 在 lithium iodide 作用下， 反应 7.0h， 以82%的产率得到3β-methoxylup-20(29)-en-28-oic acid
  参考文献：
  名称：

  Betulinic Acid Derivatives:  A New Class of Human Immunodeficiency Virus Type 1 Specific Inhibitors with a New Mode of Action

  摘要：

  A series of omega-undecanoic amides of lup-20(29)-en-28-oic acid derivatives were synthesized and evaluated for activity in CEM 4 and MT-4 cell cultures against human immunodeficiency virus type 1 (HIV-1) strain IIIB/LAI. The potent HIV inhibitors which emerged, compounds 5a, 16a, and 17b, were all derivatives of betulinic acid (3 beta-hydroxylup-20(29)-en-28-oic acid). No activity was found against HIV-2 strain ROD. Compound 5a showed no inhibition of HIV-1 reverse transcriptase activity with poly(C). oligo(dG) as template/primer, nor did it inhibit HIV-1 protease. Additional mechanistic studies revealed that this class of compounds interfere with HIV-1 entry in the cells at a postbinding step.

  DOI：

  10.1021/jm950670t

文献信息

• Triterpenoid derivatives
  申请人：——

  公开号：US20040087560A1

  公开（公告）日：2004-05-06

  The present invention relates to the use of a compound of formula (I), or a pharmaceutically acceptable salt, crystal form, complex, hydrate, or hydrolysable ester thereof, in the preparation of a medicament for treating a patient suffering from leukaemia, cancer or other proliferative disorder. A further embodiment relates to the use a compound of formula (I) in an assay for detecting the phosphorylation state of cellular substrates. The present invention also relates to novel compounds of formula (I), and the chemical synthesis thereof. 1

  本发明涉及使用式(I)的化合物，或其药用可接受的盐、结晶形式、复合物、水合物或可水解酯，在制备用于治疗患有白血病、癌症或其他增值性疾病的患者的药物中的用途。另一实施例涉及在检测细胞底物的磷酸化状态的测定中使用式(I)的化合物。本发明还涉及式(I)的新化合物及其化学合成。
• [EN] COMPOUNDS FOR REDUCING GLUCOCORTICOIDS, AND METHODS OF TREATMENT THEREOF<br/>[FR] COMPOSÉS PERMETTANT DE RÉDUIRE LES GLUCOCORTICOÏDES, ET PROCÉDÉS DE TRAITEMENT ASSOCIÉS
  申请人：BIONICHE LIFE SCIENCES INC

  公开号：WO2014071506A1

  公开（公告）日：2014-05-15

  A method for reducing glucocorticoids in an animal in need thereof comprising the use of compounds of the formula (I), wherein the definitions for R', R1-R11 and n are as disclosed in the description. The compounds of formula (I) are for the treatment or prevention of a glucocorticoid-related disorder for maintaining bone density, maintaining and improving the immune system, treating Cushing' s syndrome, treating obesity, improving reproduction efficiency, treating metabolic disorder, treating hypertension, treating hyperglycemia, treating insulin resistance, treating type 2 diabetes, and/or aiding in cancer and immune therapies

  一种用于减少需要动物体内糖皮质激素的方法，包括使用式(I)的化合物，其中R'、R1-R11和n的定义如描述中所披露。式(I)的化合物用于治疗或预防与糖皮质激素相关的疾病，以维持骨密度、维护和改善免疫系统、治疗库欣综合征、治疗肥胖、提高生殖效率、治疗代谢紊乱、治疗高血压、治疗高血糖、治疗胰岛素抵抗、治疗2型糖尿病，和/或在癌症和免疫疗法中发挥作用。
• ANTIVIRAL PHOSPHONATE ANALOGS
  申请人：Boojamra Constantine G.

  公开号：US20090275535A1

  公开（公告）日：2009-11-05

  The invention is related to phosphorus substituted compounds with antiviral activity, compositions containing such compounds, and therapeutic methods that include the administration of such compounds, as well as to processes and intermediates useful for preparing such compounds.

  这项发明涉及具有抗病毒活性的磷取代化合物，包含这种化合物的组合物以及包括给予这种化合物的治疗方法，还包括用于制备这种化合物的过程和中间体。
• BETULINIC ACID AND DERIVATIVES THEREOF USEFUL FOR THE TREATMENT OF NEUROECTODERMAL TUMORS
  申请人：Deutsches KrebsforschungszentrumStiftung des öffentlichen Rechts

  公开号：EP1124842A1

  公开（公告）日：2001-08-22
• TRITERPENOID DERIVATIVES
  申请人：Univerzita palackeho V Olomouci

  公开号：EP1292562A1

  公开（公告）日：2003-03-19