Methyl N-[3-beta-acetoxy-20(29)-en-28-oyl]-11-aminoundecanoate | 150840-96-3

• 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: Methyl N-[3-beta-acetoxy-20(29)-en-28-oyl]-11-aminoundecanoate
• 英文别名: methyl 11-[[(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-acetyloxy-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
• CAS: 150840-96-3
• 化学式: C₄₄H₇₃NO₅
• 分子量: 696.067
• InChiKey: JJBLQNXRHNJEBX-VYXZDGRQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.1
• 重原子数：
  50
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Methyl N-[3-beta-acetoxy-20(29)-en-28-oyl]-11-aminoundecanoate 在 N-溴代丁二酰亚胺(NBS) 、 四丁基溴化铵 作用下， 以 四氯化碳 、 甲苯 为溶剂， 反应 74.0h， 生成
  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：

  3Beta-乙酰氧基白桦酸 在 4-二甲氨基吡啶 、 草酰氯 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 Methyl N-[3-beta-acetoxy-20(29)-en-28-oyl]-11-aminoundecanoate
  参考文献：
  名称：

  抗艾滋病毒药物49.基于桦木酸的IC9564类似物的合成，抗HIV和抗融合活性。

  摘要：

  桦木酸衍生物IC9564抑制人免疫缺陷病毒（HIV）-1的进入。在一系列IC9564衍生物中，有5种和20种是最有希望的抗HIV感染化合物，其EC（50）值分别为0.33和0.46 microM。两种化合物抑制合胞体形成与EC（50）值分别为0.40和0.33 microM。两种测定法中可比较的EC（50）值表明，这些化合物是融合抑制剂。结构-活性关系数据还表明，可以消除IC9564中的双键，并且可以在保持抗HIV活性的同时用L-亮氨酸取代他汀类药物部分。

  DOI：

  10.1021/jm020069c

文献信息

• Anti-AIDS Agents 49. Synthesis, Anti-HIV, and Anti-Fusion Activities of IC9564 Analogues Based on Betulinic Acid
  作者：I-Chen Sun、Chin-Ho Chen、Yoshiki Kashiwada、Jiu-Hong Wu、Hui-Kang Wang、Kuo-Hsiung Lee

  DOI：10.1021/jm020069c

  日期：2002.9.1

  are fusion inhibitors. The structure-activity relationship data also indicated that a double bond in IC9564 can be eliminated and the statine moiety can be replaced with L-leucine while retaining anti-HIV activity.

  桦木酸衍生物IC9564抑制人免疫缺陷病毒（HIV）-1的进入。在一系列IC9564衍生物中，有5种和20种是最有希望的抗HIV感染化合物，其EC（50）值分别为0.33和0.46 microM。两种化合物抑制合胞体形成与EC（50）值分别为0.40和0.33 microM。两种测定法中可比较的EC（50）值表明，这些化合物是融合抑制剂。结构-活性关系数据还表明，可以消除IC9564中的双键，并且可以在保持抗HIV活性的同时用L-亮氨酸取代他汀类药物部分。
• Betulinic Acid Derivatives:  A New Class of Specific Inhibitors of Human Immunodeficiency Virus Type 1 Entry
  作者：Françoise Soler、Christèle Poujade、Michel Evers、Jean-Christophe Carry、Yvette Hénin、Anne Bousseau、Thierry Huet、Rudi Pauwels、Erik De Clercq、Jean-François Mayaux、Jean-Bernard Le Pecq、Norbert Dereu

  DOI：10.1021/jm950669u

  日期：1996.1.1

  A novel series of omega-aminoalkanoic acid derivatives of betulinic acid were synthesized and evaluated for their activity against human immunodeficiency virus (HIV). The anti-HIV-1 activity of several members of this new series was found to be in the nanomolar range in CEM 4 and MT-4 cell cultures. The optimization of the omega-aminoalkanoic acid side chain is described. The presence of an amide function within the side chain was found important for optimal activity. RPR 103611 (14g), a statine derivative, was found to be inactive against HIV-1 protease, reverse transcriptase, and integrase as well as on gp120/CD4 binding. ''Time of addition'' experiments suggested interaction with an early step of HIV-1 replication. As syncytium formation, but not virus-cell binding, seems to be affected, betulinic acid derivatives are assumed to interact with the postbinding virus-cell fusion process.
• Betulinic Acid Derivatives:  A New Class of Human Immunodeficiency Virus Type 1 Specific Inhibitors with a New Mode of Action
  作者：Michel Evers、Christèle Poujade、Françoise Soler、Yves Ribeill、Claude James、Yves Lelièvre、Jean-Christophe Gueguen、Daniel Reisdorf、Isabelle Morize、Rudi Pauwels、Erik De Clercq、Yvette Hénin、Anne Bousseau、Jean-François Mayaux、Jean-Bernard Le Pecq、Norbert Dereu

  DOI：10.1021/jm950670t

  日期：1996.1.1

  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.
• Synthesis and anti-HIV activity of bi-functional betulinic acid derivatives
  作者：Li Huang、Phong Ho、Kuo-Hsiung Lee、Chin-Ho Chen

  DOI：10.1016/j.bmc.2005.11.016

  日期：2006.4

  Betulinic acid (BA) derivatives with a side chain at C-3 can inhibit HIV-1 maturation. On the other hand, BA derivatives with a side chain at C-28 can block HIV-1 entry. In order to combine the anti-maturation and anti-entry activities in a single molecule, new bi-functional BA derivatives containing side chains at C-3 and C-28 have been synthesized. The most potent compound ([[N-[3beta-O-(3',3'-d

  在C-3处带有侧链的桦木酸（BA）衍生物可以抑制HIV-1的成熟。另一方面，在C-28带有侧链的BA衍生物可以阻止HIV-1进入。为了在单个分子中结合抗成熟和抗进入活性，已经合成了在C-3和C-28处含有侧链的新的双功能BA衍生物。最有效的化合物（[[[N- [3beta-O-（3'，3'-二甲基琥珀酰基）-lup-20（29）-en-28-oyl] -7-氨基庚基] -carba moyl]甲烷抑制HIV -1在EC26为0.0026 microM时，效力至少是抗成熟铅化合物DSB或抗进入铅化合物IC9564的20倍。这种双功能BA衍生物对HIV的进入和成熟均具有活性。