羽扇-20(30)-烯-3beta,23,28-三醇 | 84414-40-4

• 物质功能分类: 天然产物 - 萜类
• 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: 羽扇-20(30)-烯-3beta,23,28-三醇
• 中文别名: 羽扇-20(30)-烯-3BETA,23,28-三醇
• 英文名称: lup-20(29)-ene-3β,23,28-triol
• 英文别名: 23-hydroxy betulin；23-hydroxybetulin；ilekudinol；lupene-(20(29))-triol-(3β,23,28)；(3aS)-9c-Hydroxy-5at,5bc,8c,11ac-tetramethyl-3ar,8t-bis-hydroxymethyl-1t-isopropenyl-(7atH,11btH,13acH,13btH)-eicosahydro-1H-cyclopenta[a]chrysen；Lupen-(20(29))-triol-(3β,23,28)；(1R,3aS,5aR,5bR,7aR,8R,9S,11aR,11bR,13aR,13bR)-3a,8-bis(hydroxymethyl)-5a,5b,8,11a-tetramethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-ol
• CAS: 84414-40-4
• 化学式: C₃₀H₅₀O₃
• 分子量: 458.725
• InChiKey: PHMKDBZGQWXPAZ-MZFJGDBOSA-N

物化性质

• 沸点：
  557.1±15.0 °C(Predicted)
• 密度：
  1.057±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  33
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  羽扇-20(30)-烯-3beta,23,28-三醇 在 草酰氯 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  萜类化合物。三：作为糖原磷酸化酶新抑制剂的23-羟基贝丁酸衍生物的合成及生物学评价

  摘要：

  制备了一系列23-羟基甜菜酸衍生物，并作为一类新的糖原磷酸化酶（GP）抑制剂进行了体外测试。在这一系列化合物中，12b（IC 50  = 3.5μM）是最有效的GPa抑制剂。讨论了23-羟基贝丁酸衍生物的SAR初步结果。

  DOI：

  10.1016/j.bmcl.2009.10.055
• 作为产物：
  描述：

  23-hydroxybetulinic acid 在 lithium aluminium tetrahydride 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 羽扇-20(30)-烯-3beta,23,28-三醇
  参考文献：
  名称：

  WO2008/138200

  摘要：

  公开号：

文献信息

• 23-Substituted Derivatives of Lupane-type Pentacyclic Triterpenoids
  申请人：Koohang Ali

  公开号：US20100144688A1

  公开（公告）日：2010-06-10

  The present invention comprises small molecule inhibitors of cell proliferative conditions, in particular cancer and conditions associated with cancer. For example, associated malignancies include ovarian cancer, cervical cancer, breast cancer, colorectal cancer, and glioblastomas, among others. Accordingly, the compounds of the present invention are useful for treating, preventing, and/or inhibiting these diseases. Thus, the present invention also comprises pharmaceutical formulations comprising the compounds and methods of using the compounds and formulations to inhibit cancer and treat, prevent, or inhibit the foregoing diseases.

  本发明包括针对细胞增殖病症的小分子抑制剂，特别是癌症及与癌症相关的病症。例如，相关的恶性肿瘤包括卵巢癌、宫颈癌、乳腺癌、结肠直肠癌和胶质母细胞瘤等。因此，本发明的化合物可用于治疗、预防和/或抑制这些疾病。因此，本发明还包括包含这些化合物的药物配方以及使用这些化合物和配方来抑制癌症并治疗、预防或抑制上述疾病的方法。
• Preparation and Conformational Study of 19β,28-Epoxy-18α-olean-5-ene Derivatives
  作者：Martin Dračínský、Václav Richtr、Václav Křeček、Jan Sejbal、Jiří Klinot、Miloš Buděšínský

  DOI：10.1135/cccc20060387

  日期：——

  New oleanane type triterpenoids with the 5(6) double bond were prepared using partial demethylation on carbon C-4. The starting compound was 23-hydroxybetulin (1b) and the key reaction was the methylation of 19β,28-epoxy-24-nor-18α-olean-4-en-3-one (3b). The 5(6) double bond was used in preparation of new derivatives with an epoxy or oxo substituent in ring B. The conformation of ring A of new type 3-oxo oleanane derivatives with a double bond or a substituent on ring B was elucidated from vicinal coupling constants of hydrogen atoms in positions 1 and 2.

  使用部分去甲基化在碳C-4上制备了带有5(6)双键的新奥利南型三萜类化合物。起始化合物是23-羟基白桦脂（1b），关键反应是对19β,28-环氧-24-去-18α-奥利南-4-烯-3-酮（3b）进行甲基化。5(6)双键用于制备具有环B中环氧基或酮基取代基的新衍生物。通过新型3-酮基奥利南衍生物环A的构象，可以从1和2位置氢原子的邻位耦合常数中得出结论。
• Identification of Compounds with Efficacy against Malaria Parasites from Common North American Plants
  作者：Shengxin Cai、April L. Risinger、Shalini Nair、Jiangnan Peng、Timothy J. C. Anderson、Lin Du、Douglas R. Powell、Susan L. Mooberry、Robert H. Cichewicz

  DOI：10.1021/acs.jnatprod.5b00874

  日期：2016.3.25

  Some of the most valuable antimalarial compounds, including quinine and artemisinin, originated from plants. While these drugs have served important roles over many years for the treatment of malaria, drug resistance has become a widespread problem. Therefore, a critical need exists to identify new compounds that have efficacy against drug-resistant malaria strains. In the current study, extracts prepared from plants readily obtained from local sources were screened for activity against Plasmodium falciparum. Bioassay-guided fractionation was used to identify 18 compounds from five plant species. These compounds included eight lupane triterpenes (1-8), four kaempferol 3-O-rhamnosides (10-13), four kaempferol 3-O-glucosides (14-17), and the known compounds amentoflavone and knipholone. These compounds were tested for their efficacy against multi-drug-resistant malaria parasites and counterscreened against HeLa cells to measure their antimalarial selectivity. Most notably, one of the new lupane triterpenes (3) isolated from the supercritical extract of Buxus sempervirens, the common boxwood, showed activity against both drug-sensitive and-resistant malaria strains at a concentration that was 75-fold more selective for the drug-resistant malaria parasites as compared to HeLa cells. This study demonstrates that new antimalarial compounds with efficacy against drug-resistant strains can be identified from native and introduced plant species in the United States, which traditionally have received scant investigation compared to more heavily explored tropical and semitropical botanical resources from around the world.
• 839. Triterpenoids in the bark of mountain ash (sorbus aucuparia L.)
  作者：William Lawrie、John McLean、G. R. Taylor

  DOI：10.1039/jr9600004303

  日期：——
• RICHTR, VACLAV;KLINOT, JIRI, SB. PED. FAK. PLZNI. CHEM.,(1990) C. 37-52
  作者：RICHTR, VACLAV、KLINOT, JIRI

  DOI：——

  日期：——