methyl dihydrobetulonate | 20066-05-1

• 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 dihydrobetulonate
• 英文别名: methyl (1S,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-9-oxo-1-propan-2-yl-2,3,4,5,6,7,7a,10,11,11b,12,13,13a,13b-tetradecahydro-1H-cyclopenta[a]chrysene-3a-carboxylate
• CAS: 20066-05-1
• 化学式: C₃₁H₅₀O₃
• 分子量: 470.736
• InChiKey: DFCFXNDZRVOAHX-DSBZJMBESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  34
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl dihydrobetulonate 在 sodium hydroxide 、 苯基氯化硒 、 双氧水 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 生成 methyl (1R,2R,5S,8S,9R,10R,13S,14R,15R,17R,20R)-1,2,14,19,19-pentamethyl-18-oxo-8-propan-2-yl-16-oxahexacyclo[11.9.0.02,10.05,9.014,20.015,17]docosane-5-carboxylate
  参考文献：
  名称：

  Synthesis and cytotoxic activity of a-ring modified betulinic acid derivatives

  摘要：

  New A-ring modified betulinic acid derivatives having small steric hindrance were prepared and tested for cytotoxic activity on 3 cancer cell lines: 10 compounds showed stronger cytotoxic activity than betulinic acid. Especially, the compounds bearing 1-ene-3-oxo with electron-withdrawing groups at C2 showed strong cytotoxicity. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00724-8
• 作为产物：
  描述：

  白桦脂酸 在 铂 chromium(VI) oxide 、 氢气 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 氯仿 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 生成 methyl dihydrobetulonate
  参考文献：
  名称：

  Triterpenoid Pyrazines and Benzopyrazines with Cytotoxic Activity

  摘要：

  Twelve lupane, 18 alpha-oleanane, and des-E-lupane derivatives (1a-5b) were either extracted from natural sources or synthesized from betulinic acid (1a) and betulin (2). Compounds 1b, 1c, 3b, 3c, 4b, 4c, 5a, and 5b were then used as starting materials for further synthesis of a series of pyrazines and benzopyrazines (6a-18); 20 of them are new (6a-6e, 7a-7d, and 10a-18). Activity of pyrazine 6a against the T-lymphoblastic leukemia cell line CEM encouraged us to synthesize several new esters (6b-6d) to study structure-activity relationships with respect to substitution of the carboxyl group at position 28. The synthesized compounds were tested for cytotoxicity against a variety of cancer cell lines of different histogenetic origin, and the results were compared with cytotoxicity of the known starting compounds. Significant cytotoxic activity against A 549, K 562, and multidrug-resistant K 562-tax cell lines was found in pyrazines 6a, 6d, and 6e.

  DOI：

  10.1021/np060436d

文献信息

• Reactions in high boiling solvent—II
  作者：S.B. Mahato、S.K. Banerjee、R.N. Chakravarti

  DOI：10.1016/s0040-4020(01)92409-3

  日期：——

  The effect of Raney nickel on triterpenoids in boiling p-cymene has been studied. The following three different types of reactions have been observed: (a) dehydrogenation (oxidation) of the 3-OH group, (b) saturation of the easily reducible double bond, and (c) shifting of the double bond to an adjacent position as in allylic shift. The shift is of reversible nature. A 3-hydroxytriterpenehydrochloride

  研究了阮内镍对沸腾对甲基苯丙醚中三萜类化合物的影响。已经观察到以下三种不同类型的反应：（a）3-OH基团的脱氢（氧化），（b）易还原双键的饱和，以及（c）双键转移至相邻位置在盟友转移中。这种转变具有可逆性。通过该反应，将3-羟基三萜烯盐酸盐转化为3-酮-三萜烯，通过氢解除去Cl原子。还提出了一种机制。
• Synthesis of lupane triterpenoids with triphenylphosphonium substituents and studies of their antitumor activity
  作者：A. Yu. Spivak、D. A. Nedopekina、E. R. Shakurova、R. R. Khalitova、R. R. Gubaidullin、V. N. Odinokov、U. M. Dzhemilev、Yu. P. Bel’skii、N. V. Bel’skaya、S. A. Stankevich、E. V. Korotkaya、V. A. Khazanov

  DOI：10.1007/s11172-013-0028-y

  日期：2013.1

  New derivatives of lupane triterpenoids, viz., 20,29-dihydrobetulinic and 3-epi-20,29-dihydrobetulinic acid derivatives containing triphenylphosphonium fragments as substituents were synthesized. These compound considerably exceed betulinic acid in antitumor activity.

  合成了羽扇烷三萜类新衍生物，即含有三苯基鏻片段作为取代基的20,29-二氢桦木酸和3-表-20,29-二氢桦木酸衍生物。这些化合物的抗肿瘤活性大大超过桦木酸。
• Synthesis of 3-Methyl Derivatives from Dihydrobetulonic Acid Methyl Ester
  作者：G. F. Krainova、Yu. A. Beloglazova、V. V. Grishko

  DOI：10.1007/s10600-023-03923-x

  日期：——

  A 2,3-secotriterpenoid with a methylketone was prepared from 1-hydroxyiminodihydrobetulonic acid methyl ester via a Grignard reaction followed by a Beckmann rearrangement. Functionalization of it led to the formation of 3-hydroxy- and 31-bromo-substituted derivatives; intramolecular cyclization, to the formation of a five-membered ring A with an alkene-nitrile. The synthetic products included compounds

  通过格氏反应和贝克曼重排，从 1-羟基亚氨基二氢白桦甲酸甲酯制备了带有甲基酮的 2,3-环三萜类化合物。它的功能化导致形成 3-羟基和 31-溴代衍生物；分子内环化，与烯烃-腈形成五元环A。合成产物包括对 MCF-7、HCT116、A549 和 PC-3 癌细胞具有中等细胞毒性 (IC 50 25.22–46.66 μM) 的化合物（ 5a和9 ）。
• Effect of modification of betulinic acid at the C3-carbon atom of homolupane triterpenoids on the antiproliferative activity in vitro
  作者：Lucie Rárová、Zbigniew Pakulski、Miroslav Strnad、Marie Kvasnicová、Tereza Štenclová、Piotr Cmoch

  DOI：10.1016/j.jsbmb.2022.106161

  日期：2022.11

  In search of new cytotoxic derivatives based on the lupane scaffold, methyl betulonate and methyl 20,29-dihydrobetulonate were conjugated with Reformatsky reagents to provide homolupanes extended at the C3-carbon atom. Further transformations of the functional groups afforded a series of derivatives with 2-hydroxyethyl and allyl alcohol moieties. Their varying antiproliferative activity in vitro was

  为了寻找基于羽扇烷支架的新型细胞毒性衍生物，将白桦酸甲酯和 20,29-二氢榍榫酸甲酯与 Reformatsky 试剂偶联，以提供在 C3-碳原子处延伸的均香涴烷。官能团的进一步转化提供了一系列具有 2-羟乙基和烯丙基醇部分的衍生物。然后在四种癌细胞系和正常人 BJ 成纤维细胞中研究它们在体外不同的抗增殖活性。在宫颈癌 HeLa 细胞中，衍生物 5 、 6 和 17 最有前途，微摩尔 IC较低 50秒，对成纤维细胞无毒性，因此显示出较高的治疗指数。此外，用化合物 5、6、13 和 29 处理 24 小时后，在 HeLa 细胞中发现诱导细胞凋亡。这个新合成的系列比已发表的 lupane 和 homolupane 三萜和皂苷更有趣，因为它们对健康人体细胞无毒，对各种癌细胞系具有更强的细胞毒性。这种方法增加了它们作为抗癌剂的潜力。
• Synthesis of 2,3-Seco-Derivatives of Dihydrobetulonic Acid and its Methyl Ester
  作者：G. F. Krainova、O. N. Gagarskikh、V. V. Grishko

  DOI：10.1007/s10600-022-03770-2

  日期：2022.7

  2,3-Secolupane aldehydonitriles with an isopropyl fragment were synthesized via Beckman fragmentation of ring A of triterpene α-hydroxyoximes obtained from dihydrobetulonic acid and its methyl ester. Redox transformation of the aldehydonitriles at C-3 led to the formation of the corresponding 3-hydroxy- and 3-carboxy-derivatives. The MTT assay found that only the triterpene oximes possessed moderate

  具有异丙基片段的 2,3-Secolupane 醛腈是通过对从二氢松香酸及其甲酯获得的三萜α-羟基肟的 A 环进行贝克曼断裂合成的。醛腈在 C-3 处的氧化还原转化导致形成相应的 3-羟基和 3-羧基衍生物。MTT 分析发现，合成产物中只有三萜肟对 HCT 116、RD TE32、MS 和 PC-3 肿瘤细胞具有中等的细胞毒活性（IC50 27.8–61.7 μM）。