6-{[(3β)-3-羟基-28-羰基羽扇-20(29)-烯-28-基]氨基}己酸 | 150840-27-0

• 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
• 中文名称: 6-{[(3β)-3-羟基-28-羰基羽扇-20(29)-烯-28-基]氨基}己酸
• 英文名称: N-(3beta-Hydroxylup-20(29)-en-28-oyl)-6-aminohexanoic acid
• 英文别名: 6-[[(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-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]hexanoic acid
• CAS: 150840-27-0
• 化学式: C₃₆H₅₉NO₄
• 分子量: 569.869
• InChiKey: QWFPGBOVYVBGPD-WUNWLKNYSA-N

物化性质

• 沸点：
  695.7±48.0 °C(Predicted)
• 密度：
  1.067±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  41
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  86.6
• 氢给体数：
  3
• 氢受体数：
  4

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  白桦脂酸	Betulinic acid	472-15-1	C30H48O3	456.709
  路路通酸	betulonic acid	4481-62-3	C30H46O3	454.693
  白桦脂醇	betulin	473-98-3	C30H50O2	442.726

反应信息

• 作为反应物：
  描述：

  L-丙氨酸甲酯盐酸盐 、 6-{[(3β)-3-羟基-28-羰基羽扇-20(29)-烯-28-基]氨基}己酸 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Betulinic Acid Derivatives as Human Immunodeficiency Virus Type 2 (HIV-2) Inhibitors

  摘要：

  We previously reported that [[N-[3 beta-hydroxyllup-20(29)-en-28-oyl]-7-aminoheptyl]carbamoyl]methane (A43D, 4) was a potent HIV-1 entry inhibitor. However, 4 was inactive against HIV-2 virus, suggesting the structural requirements for targeting these two retroviruses are different. In this study, a series of new betulinic acid derivatives were synthesized, and some of them displayed selective anti-HIV-2 activity at nanomolar concentrations. In comparison to compounds with anti-HIV-1 activity, a shorter C-28 side chain is required for optimal anti-HIV-2 activity.

  DOI：

  10.1021/jm9004253
• 作为产物：
  描述：

  6-氨基己酸甲酯 盐酸盐 在 sodium hydroxide 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 6-{[(3β)-3-羟基-28-羰基羽扇-20(29)-烯-28-基]氨基}己酸
  参考文献：
  名称：

  Betulinic Acid Derivatives:  A New Class of Specific Inhibitors of Human Immunodeficiency Virus Type 1 Entry

  摘要：

  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.

  DOI：

  10.1021/jm950669u

文献信息

• Synthesis of Novel Pentacyclic Triterpenoid Derivatives that Induce Apoptosis in Cancer Cells through a ROS-dependent, Mitochondrial-Mediated Pathway
  作者：Boyang Cheng、Xindang Chu、Ruiwen Liu、Xinyuan Ma、Mengyang Wang、Jiayi Zhang、Pingxuan Jiao、Qianqian Gao、Wenxiao Ma、Yongmin Zhang、Chuanke Zhao、Demin Zhou、Sulong Xiao

  DOI：10.1021/acs.molpharmaceut.2c00885

  日期：2023.1.2

  indicating the activation of the intrinsic apoptosis pathway. Furthermore, 48 dramatically induced the generation of reactive oxygen species (ROS) in HL-60 cells, and the corresponding effect could be reversed using the ROS scavenger N-acetylcysteine. Collectively, these results suggest that the novel pentacyclic triterpenoid derivatives trigger the intrinsic apoptotic pathways via the ROS-mediated activation

  桦木酸 (BA) 和齐墩果酸 (OA) 是植物衍生的结合物，存在于各种药用植物中，已成为潜在的抗肿瘤药物。在此，通过与全O-甲基化-β-环糊精 (PM-β-CD)缀合合成了一系列新型 BA 和 OA 衍生物，并评估了它们对一组三种人类癌细胞系的抗癌特性。观察到两种 OA-PM-β-CD 缀合物（48和50）是针对三种细胞系（MCF-7、BGC-823 和 HL-60）的最有效缀合物，具有 15 至 20 倍IC 50值降低（IC 50: 6.06–8.47 μM) 与其亲本偶联物 (OA) 相比。膜联蛋白 V-FITC/碘化丙啶染色和蛋白质印迹分析表明，两种结合物均能诱导 HL-60 细胞凋亡。此外，在代表性缀合物48处理的 HL-60 细胞中，观察到线粒体膜电位降低和随后细胞色素c释放到胞质溶胶中，表明内在凋亡途径的激活。此外，48显着诱导 HL-60 细胞中活性氧 (ROS) 的产生，并且使用
• 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 as Human Immunodeficiency Virus Type 2 (HIV-2) Inhibitors
  作者：Zhao Dang、Weihong Lai、Keduo Qian、Phong Ho、Kuo-Hsiung Lee、Chin-Ho Chen、Li Huang

  DOI：10.1021/jm9004253

  日期：2009.12.10

  We previously reported that [[N-[3 beta-hydroxyllup-20(29)-en-28-oyl]-7-aminoheptyl]carbamoyl]methane (A43D, 4) was a potent HIV-1 entry inhibitor. However, 4 was inactive against HIV-2 virus, suggesting the structural requirements for targeting these two retroviruses are different. In this study, a series of new betulinic acid derivatives were synthesized, and some of them displayed selective anti-HIV-2 activity at nanomolar concentrations. In comparison to compounds with anti-HIV-1 activity, a shorter C-28 side chain is required for optimal anti-HIV-2 activity.