(3β,7β,23R)-7-methoxycucurbita-5,24-diene-3,23-diol | 922192-67-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (3β,7β,23R)-7-methoxycucurbita-5,24-diene-3,23-diol
• 英文别名: karavilagenin C；karavelagenin C；(3S,7S,8R,9S,10S,13R,14S,17R)-17-[(2R,4R)-4-hydroxy-6-methylhept-5-en-2-yl]-7-methoxy-4,4,9,13,14-pentamethyl-2,3,7,8,10,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol
• CAS: 922192-67-4
• 化学式: C₃₁H₅₂O₃
• 分子量: 472.752
• InChiKey: MTYMFIWYWSHNSU-NLUPGCNDSA-N

物化性质

• 沸点：
  555.4±40.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  丁酸酐 、 (3β,7β,23R)-7-methoxycucurbita-5,24-diene-3,23-diol 在 吡啶 作用下， 反应 72.0h， 以26 mg的产率得到(23R)-3β,23-dibutanoyloxy-7β-methoxycucurbita-5,24-diene
  参考文献：
  名称：

  Karavilagenin C衍生物作为抗疟药

  摘要：

  Karavilagenin C（1）是葫芦烷型三萜类化合物，先前从苦瓜苦瓜的地上部分中分离出来，用不同的烷酰基，芳酰基和肉桂酰氯/杂化物酰化，生成十种新的单酯或二酯，karavoates F（7）和HP（8 – 16）。此外，从同一植物中分离出新的化合物葫芦巴胺醇C（17）。通过光谱方法（包括2D NMR实验）指定了它们的结构。化合物1和17和酰基衍生物8 - 16沿与其他五个酯（2 - 6，从1开始制备的karavoates A–E）在体外对恶性疟原虫的氯喹敏感性（3D7）和氯喹抗性（Dd2）菌株具有体外抗疟活性。化合物1表现出中等活性，而17是无活性的。但是，对于大多数卡拉维加宁C烷酰基和单芳酰基/肉桂酰基衍生物，观察到了显着的抗疟原虫活性。卡拉沃酸盐B，D，E，I和M最活跃，显示出与氯喹相似的IC 50值，尤其是抗药性菌株（IC 50<0.6μM）。讨论了构效关系（SAR）。此外，朝向化合物的人类细胞的初步毒性1

  DOI：

  10.1016/j.bmc.2010.11.015

文献信息

• Triterpenoids from Momordica balsamina: Reversal of ABCB1-mediated multidrug resistance
  作者：Cátia Ramalhete、Silva Mulhovo、Joseph Molnar、Maria-José U. Ferreira

  DOI：10.1016/j.bmc.2016.08.022

  日期：2016.11

  The ability as P-glycoprotein (P-gp, ABCB1) modulators of thirty (1-30) triterpenoids of the cucurbitane-type was evaluated on human L5178 mouse T-lymphoma cell line transfected with the human MDR1 gene, through the rhodamine-123 exclusion assay. Compounds (1-26, and 29, 30) were previously obtained from the African medicinal plant Momordica balsamina, through both isolation (1-15) and molecular derivatization (16-26 and 29, 30). Compounds 27-28 are two new karavilagenin C (34) derivatives having succinic acid moieties. Apart from 4, 6, 8, 10 and 11, most of the isolated compounds (1-15) displayed strong MDR reversing activity in a dose-dependent mode, exhibiting a many-fold activity when compared with verapamil, used as positive control. At the lowest concentration tested, compounds 2 and 7 were the most active. However, a decrease of activity was found for the acyl derivatives (16-30). In a chemosensitivity assay, the MDR reversing activity of some of the most active compounds (1-3, 5, 7, 12-15) was further assessed on the same cell model. All the tested compounds, excepting 15, corroborated the results of the transport assay, revealing to synergistically interact with doxorubicin. Structure-activity relationship studies, taking into account previous results, showed that different substitution patterns, at both the tetracyclic nucleus and the side chain, play important role in ABCB1 reversal activity. An optimal lipophilicity was also recognized. (C) 2016 Elsevier Ltd. All rights reserved.
• New potent P-glycoprotein modulators with the cucurbitane scaffold and their synergistic interaction with doxorubicin on resistant cancer cells
  作者：Cátia Ramalhete、Joseph Molnár、Silva Mulhovo、Virgílio E. Rosário、Maria-José U. Ferreira

  DOI：10.1016/j.bmc.2009.08.020

  日期：2009.10

  The novel cucurbitacins, balsaminagenin A and B (1-2) and balsaminoside A (3) and the know cucurbitacin karavelagenin C (4), together with five new mono or diacylated derivatives (5-9) of karavelagenin C were evaluated for multidrug resistance reversing activity on human MDR1 gene transfected mouse lymphoma cells. Compounds 2-6 exhibited a strong activity compared with that of the positive control, verapamil. Structure-activity relationships are discussed. Moreover, in the checkerboard model of combination chemotherapy, the interaction between doxorubicin and compounds 2-5 synergistically enhanced the effect of the anticancer drug. Compounds 1-4 were isolated from the aerial parts of Momordica balsamina L. The structures of the compounds were established on the basis of spectroscopic methods including 2D NMR experiments (COSY, HMQC, HMBC and NOESY). (C) 2009 Elsevier Ltd. All rights reserved.
• Karavilagenin C derivatives as antimalarials
  作者：Cátia Ramalhete、Dinora Lopes、Joseph Molnár、Silva Mulhovo、Virgílio E. Rosário、Maria-José U. Ferreira

  DOI：10.1016/j.bmc.2010.11.015

  日期：2011.1

  with different alkanoyl, aroyl and cinnamoyl chlorides/anydrides, yielding ten new mono or diesters, karavoates F (7) and H-P (8–16). Furthermore, the new compound cucurbalsaminol C (17) was isolated from the same plant. Their structures were assigned by spectroscopic methods, including 2D NMR experiments. Compounds 1 and 17 and the acyl derivatives 8–16 along with other five esters (2–6, karavoates A–E)

  Karavilagenin C（1）是葫芦烷型三萜类化合物，先前从苦瓜苦瓜的地上部分中分离出来，用不同的烷酰基，芳酰基和肉桂酰氯/杂化物酰化，生成十种新的单酯或二酯，karavoates F（7）和HP（8 – 16）。此外，从同一植物中分离出新的化合物葫芦巴胺醇C（17）。通过光谱方法（包括2D NMR实验）指定了它们的结构。化合物1和17和酰基衍生物8 - 16沿与其他五个酯（2 - 6，从1开始制备的karavoates A–E）在体外对恶性疟原虫的氯喹敏感性（3D7）和氯喹抗性（Dd2）菌株具有体外抗疟活性。化合物1表现出中等活性，而17是无活性的。但是，对于大多数卡拉维加宁C烷酰基和单芳酰基/肉桂酰基衍生物，观察到了显着的抗疟原虫活性。卡拉沃酸盐B，D，E，I和M最活跃，显示出与氯喹相似的IC 50值，尤其是抗药性菌株（IC 50<0.6μM）。讨论了构效关系（SAR）。此外，朝向化合物的人类细胞的初步毒性1