Squamocin D | 156199-51-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Squamocin D
• 英文别名: Asiminacin；squamocin；Rel-squamocin；(2S)-4-[(13R)-13-[(2R,5R)-5-[(2R,5R)-5-[(1R,5S)-1,5-dihydroxyundecyl]oxolan-2-yl]oxolan-2-yl]-13-hydroxytridecyl]-2-methyl-2H-furan-5-one
• CAS: 156199-51-8
• 化学式: C₃₇H₆₆O₇
• 分子量: 622.927
• InChiKey: DAEFUOXKPZLQMM-WGCJABNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  44
• 可旋转键数：
  25
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  甲氧基-三氟甲基苯 、 Squamocin D 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 4.0h， 生成
  参考文献：
  名称：

  The absolute configuration of adjacent bis-THF acetogenins and asiminocin, a novel highly potent asimicin isomer from Asimina triloba

  摘要：

  A novel acetogenin, asiminocin (1), was isolated by activity-directed fractionation from the stem bark of the paw paw tree, Asimina triloba. By spectral and chemical methods, 1 was identified as (30S)-hydroxy-4-deoxyasimicin. The absolute configuration of 1, along with those of previously reported acetogenins asimin, asiminacin, bullatin, (30S)-bullanin, and (30R) bullanin, was determined by Mosher ester methodology. Compound 1 was highly inhibitory to three human solid tumor cell lines with over a billion times the potency of adriamycin.

  DOI：

  10.1016/0968-0896(95)00155-7
• 作为产物：
  描述：

  (S)-(+)-1-Decen-3-ol 在 10percent Pd/c 吡啶 、 咪唑 、 2,6-二甲基吡啶 、 sodium hydroxide 、 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 、 草酰氯 、 氢气 、 三甲基乙酰氯 、 双(三甲基硅烷基)氨基钾 、 magnesium 、 二甲基亚砜 、 1,2-二溴乙烷 、 三乙胺 、 lithium chloride 、 lithium bromide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 水 、 异丙醇 、 甲苯 、 叔丁醇 为溶剂， 反应 68.08h， 生成 Squamocin D
  参考文献：
  名称：

  Total Syntheses of Squamocin A and Squamocin D, Bi-tetrahydrofuran Acetogenins from Annonaceae

  摘要：

  DOI：

  10.1002/(sici)1099-0690(200005)2000:10<1889::aid-ejoc1889>3.0.co;2-r

文献信息

• Total syntheses of squamocin A and squamocin D
  作者：Ulrich Emde、Ulrich Koert

  DOI：10.1016/s0040-4039(99)01225-3

  日期：1999.8

  The total syntheses of two acetogenins, squamocin A and squamocin D, have been achieved. The adjacent bis-THF subunit was constructed by a multiple Williamson reaction. The left and the right side chain were added by addition of organomagnesium compounds to aldehyde functions. The conversion of a carboxylic acid into the butenolide moiety concluded both syntheses. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Asimin, Asiminacin, and Asiminecin: Novel Highly Cytotoxic Asimicin Isomers from Asimina triloba
  作者：Geng-Xian Zhao、Laura R. Miesbauer、David L. Smith、Jerry L. McLaughlin

  DOI：10.1021/jm00039a009

  日期：1994.6

  Activity-directed fractionation of the stem bark extracts of the North American paw paw tree, Asimina triloba (Annonaceae), has yielded three further acetogenins: asimin (2), asiminacin (3), and asiminecin (4). 2-4 are structural isomers of asimicin (1), which is a potent inhibitor of mitochondrial NADH:ubiquinone oxidoreductase, and thus exhibits potent antitumor and pesticidal effects. 2-4 have the same carbon skeleton and configurations as those of 1, but they have the third hydroxyl group located at C-10, C-28, and C-29, respectively, rather than at C-4. The determinations of the hydroxyl group locations were largely based on mass spectral analyses of TMSi and TMSi-d(9) derivatives. 2-4 all showed highly potent cytotoxicities (ED(50) values as low as <10(-12) mu g/mL) with notable selectivities for the HT-29 human colon cancer cell line. The presence of a third hydroxyl at C-4, C-10, C-28, or C-29, as in 1-4, greatly enhances the bioactivity of 4-deoxyasimicin (5).
• Total Syntheses of Squamocin A and Squamocin D, Bi-tetrahydrofuran Acetogenins from Annonaceae
  作者：Ulrich Emde、Ulrich Koert

  DOI：10.1002/(sici)1099-0690(200005)2000:10<1889::aid-ejoc1889>3.0.co;2-r

  日期：2000.5
• The absolute configuration of adjacent bis-THF acetogenins and asiminocin, a novel highly potent asimicin isomer from Asimina triloba
  作者：Geng-Xian Zhao、Jin-Feng Chao、Lu Zeng、Matthew J. Rieser、Jerry L. McLaughlin

  DOI：10.1016/0968-0896(95)00155-7

  日期：1996.1

  A novel acetogenin, asiminocin (1), was isolated by activity-directed fractionation from the stem bark of the paw paw tree, Asimina triloba. By spectral and chemical methods, 1 was identified as (30S)-hydroxy-4-deoxyasimicin. The absolute configuration of 1, along with those of previously reported acetogenins asimin, asiminacin, bullatin, (30S)-bullanin, and (30R) bullanin, was determined by Mosher ester methodology. Compound 1 was highly inhibitory to three human solid tumor cell lines with over a billion times the potency of adriamycin.