allobetulone | 125225-30-1

• 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: allobetulone
• 英文别名: (1R,4R,5R,8R,13R,14R,17R,18S,19R)-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[17.3.2.01,18.04,17.05,14.08,13]tetracosan-10-one
• CAS: 125225-30-1
• 化学式: C₃₀H₄₈O₂
• 分子量: 440.71
• InChiKey: XGDVSJLOTVQNKY-UDGNTYHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  32
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  allobetulone 在 potassium tert-butylate 、 亚硝酸异戊酯 作用下， 以 叔丁醇 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Synthesis and Intramolecular Cyclization of a 2,3-seco-Oleanane Triterpenoid with an Ethylketone Fragment

  摘要：

  合成了 1-氰基-2,3-seco-18αH-油烷 3-乙基-3-酮，并在碱催化下进行了分子内氧代腈 C(1)-C(3) 环化反应，生成了 A-五环 1-氰基-3-乙基-1(3)-烯。研究了合成化合物对肿瘤细胞系 HEp-2、HCT 116、MS、RD TE32、A549、MCF-7 和 PC3 培养物的细胞毒性。

  DOI：

  10.1007/s10600-018-2564-z
• 作为产物：
  描述：

  白桦脂醇 在 sodium dichromate 、 montmorrillonite K₁₀ 、 sodium acetate 、 乙酸酐 作用下， 以 氯仿 、 水 、 溶剂黄146 、 甲苯 为溶剂， 反应 49.0h， 生成 allobetulone
  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

• Synthesis of spiro[(6-phenyl-3,4-dihydro-2H-1,3-dioxine)-2R(S), 3′-(19′,28′-oxidooleanan)]-4-ones and X-ray diffraction analysis of their configuration
  作者：T. V. Rybalova、Yu. V. Gatilov、D. D. Nekrasov、A. E. Rubtsov、A. G. Tolstikov

  DOI：10.1007/s10947-006-0256-1

  日期：2005.11

  The structure of two stereoisomeric spiroadducts of allobetulone with 5-phenyl-2,3-dihydrofuran-2,3-dione was established by X-ray diffraction (XRD) analysis. The crystals of the 2R isomer are orthorhombic, P212121, a = 10.825(5) Å, b = 12.849(6) Å, c = 23.358(9) Å; V = 3249(2) Å3, Z = 4, d calc = 1.200 g/cm3; the crystals of the 2S isomer hemihydrate are triclinic, P1, a = 11.505(7) Å, b = 12.192(8) Å, c = 13.123(8) Å; α = 103.35(5)°, β = 100.80(5)°, γ = 90.98(5)°; V = 1756(2) Å3, Z = 2, d calc = 1.127 g/cm3. The molecular structure of the spiroadducts is discussed.

  通过 X 射线衍射（XRD）分析，确定了阿洛贝杜酮与 5-苯基-2,3-二氢呋喃-2,3-二酮的两种立体异构体的衍生产品结构。2R 异构体的晶体为正方晶，P212121，a = 10.825(5)埃，b = 12.849(6)埃，c = 23.358(9)埃；V = 3249(2)埃3，Z = 4，d calc = 1.200 g/cm3；2S 异构体半水合物的晶体为三菱形，P1，a = 11.505(7) Å，b = 12.192(8) Å，c = 13.123(8) Å；α = 103.35(5)° ，β = 100.80(5)° ，γ = 90.98(5)° ；V = 1756(2) Å3 ，Z = 2 ，d calc = 1.127 g/cm3。讨论了螺roadducts 的分子结构。
• Triterpenoid pyrazines and pyridines – Synthesis, cytotoxicity, mechanism of action, preparation of prodrugs
  作者：Jiří Hodoň、Ivo Frydrych、Zdeňka Trhlíková、Jan Pokorný、Lucie Borková、Sandra Benická、Martin Vlk、Barbora Lišková、Agáta Kubíčková、Martina Medvedíková、Martin Pisár、Jan Šarek、Viswanath Das、Anna Ligasová、Karel Koberna、Petr Džubák、Marián Hajdúch、Milan Urban

  DOI：10.1016/j.ejmech.2022.114777

  日期：2022.12

  A set of fifteen triterpenoid pyrazines and pyridines was prepared from parent triterpenoid 3-oxoderivatives (betulonic acid, dihydrobetulonic acid, oleanonic acid, moronic acid, ursonic acid, heterobetulonic acid, and allobetulone). Cytotoxicity of all compounds was tested in eight cancer and two non-cancer cell lines. Evaluation of the structure-activity relationships revealed that the triterpenoid

  由母体三萜类 3-氧代衍生物（桦木酸、二氢桦木酸、齐墩果酸、木糖酸、熊果酸、杂桦木酸和别木酮）制备了一组十五种三萜类吡嗪和吡啶。在八种癌症和两种非癌细胞系中测试了所有化合物的细胞毒性。对构效关系的评估表明，三萜核心决定了最终分子是否具有活性，而杂环能够增加活性并调节特异性。五种化合物（1b、1c、2b、2c和8）被发现具有优先和高度细胞毒性（IC 50 ≈ 1 μM) 抗白血病癌细胞系（CCRF-CEM、K562、CEM-DNR 或 K562-TAX）。令人惊讶的是，化合物1c、2b和2c在耐多药白血病细胞（CEM-DNR 和 K562-TAX）中的活性比在其非耐药类似物（CCRF-CEM 和 K562）中的活性高 10 倍。测量了最有希望的候选药物的药理参数，并合成了两种类型的前药：1）含糖缀合物，其中大部分具有改善细胞穿透性并在 CCRF-CEM 细胞系中保持高细胞毒性，不幸的是，它们失去了对抗性细胞。2)
• Sejbal, Jan; Klinot, Jiri; Hrncirova, Daniela, Collection of Czechoslovak Chemical Communications, 1985, vol. 50, # 12, p. 2753 - 2759
  作者：Sejbal, Jan、Klinot, Jiri、Hrncirova, Daniela、Vystrcil, Alois

  DOI：——

  日期：——
• LUGEMWA, FULGENTIUS N.;HUANG, FU-YUNG;BENTLEY, MICHAEL D.;MENDEL, MICHAEL+, J. AGR. AND FOOD CHEM., 38,(1990) N, C. 493-496
  作者：LUGEMWA, FULGENTIUS N.、HUANG, FU-YUNG、BENTLEY, MICHAEL D.、MENDEL, MICHAEL+

  DOI：——

  日期：——
• Hase, T. A.; Suokas, E.; Weckman, A., Synthetic Communications, 1981, vol. 11, # 6, p. 489 - 492
  作者：Hase, T. A.、Suokas, E.、Weckman, A.

  DOI：——

  日期：——