demethylincisterol A₃ | 166318-86-1

• 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: demethylincisterol A₃
• 英文别名: (17R)-4-hydroxy-17-methylincisterol；(3aS,5aR,6R,8aR)-3a-Hydroxy-5a-methyl-6-[(1R,2E,4R)-1,4,5-trimethyl-2-hexen-1-yl]-3a,4,5,5a,6,7,8,8a-octahydro-2H-cyclopenta[e]benzofuran-2-one；(3aS,5aR,6R,8aR)-6-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-3a-hydroxy-5a-methyl-4,5,6,7,8,8a-hexahydrocyclopenta[e][1]benzofuran-2-one
• CAS: 166318-86-1
• 化学式: C₂₁H₃₂O₃
• 分子量: 332.483
• InChiKey: UINDYEKBRZRPSX-QPLMFNHESA-N

物化性质

• 沸点：
  474.7±33.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 demethylincisterol A₃ 以86%的产率得到C₂₃H₃₄O₄
  参考文献：
  名称：

  4-hydroxy-17-methylincisterol, an inhibitor of DNA polymerase-α activity and the growth of human cancer cells in vitro

  摘要：

  An ergosterol derivative, 4-hydroxy-17-methylincisterol (HMI), was found to be an inhibitor of mammalian DNA polymerases in vitro. HMI inhibited the activity of calf thymus DNA polymerase alpha (pol. alpha). Among the polymerases tested, pol. alpha was the most sensitive to inhibition by HMI, and the inhibition was concentration dependent. The inhibitory effect of HMI on pol. a was almost the same as that shown by aphidicolin, a well known potent pol. alpha inhibitor. HMI had relatively less effect on rat DNA pol. beta, human immunodeficiency virus type 1 reverse transcriptase (HIV-RT), and calf thymus terminal deoxynucleotidyl transferase (TdT) in vitro, and did not influence the activities of prokaryotic DNA polymerases such as Klenow Fragment of DNA polymerase I, or the DNA-metabolic enzyme DNase I. HMI was found to be able to prevent the growth of human cancer cell lines originating from patients with leukemia or various solid tumors; its IC50 values ranged from 7.5 to 12 mu M. We also synthesized other ergosterol derivatives and tested them, and found that two compounds, 17-methylincisterol and 4-acetyl-17-methylincisterol, have similar inhibitory effects. (C) 1998 Elsevier Science Inc.

  DOI：

  10.1016/s0006-2952(98)00197-x
• 作为产物：
  描述：

  麦角固醇 以 氯仿 为溶剂， 反应 9.0h， 以3.6 mg的产率得到demethylincisterol A₃
  参考文献：
  名称：

  4-hydroxy-17-methylincisterol, an inhibitor of DNA polymerase-α activity and the growth of human cancer cells in vitro

  摘要：

  An ergosterol derivative, 4-hydroxy-17-methylincisterol (HMI), was found to be an inhibitor of mammalian DNA polymerases in vitro. HMI inhibited the activity of calf thymus DNA polymerase alpha (pol. alpha). Among the polymerases tested, pol. alpha was the most sensitive to inhibition by HMI, and the inhibition was concentration dependent. The inhibitory effect of HMI on pol. a was almost the same as that shown by aphidicolin, a well known potent pol. alpha inhibitor. HMI had relatively less effect on rat DNA pol. beta, human immunodeficiency virus type 1 reverse transcriptase (HIV-RT), and calf thymus terminal deoxynucleotidyl transferase (TdT) in vitro, and did not influence the activities of prokaryotic DNA polymerases such as Klenow Fragment of DNA polymerase I, or the DNA-metabolic enzyme DNase I. HMI was found to be able to prevent the growth of human cancer cell lines originating from patients with leukemia or various solid tumors; its IC50 values ranged from 7.5 to 12 mu M. We also synthesized other ergosterol derivatives and tested them, and found that two compounds, 17-methylincisterol and 4-acetyl-17-methylincisterol, have similar inhibitory effects. (C) 1998 Elsevier Science Inc.

  DOI：

  10.1016/s0006-2952(98)00197-x

文献信息

• Biomimetic Synthesis of Chaxine and its Related Compounds
  作者：Misaki Niki、Yushi Hirata、Atsuo Nakazaki、Jing Wu、Hirokazu Kawagishi、Toshio Nishikawa

  DOI：10.1021/acs.joc.9b03482

  日期：2020.4.3

  The highly oxidized natural products chaxine B and BB have been synthesized from ergosterol in eight steps according to a route inspired by their proposed biosynthesis; key steps were an oxidative cascade from a furan intermediate to an enol ester using MCPBA, followed by diastereoselective epoxidation and acyloxy migration. This concise synthesis resulted in the revision of the structures of chaxine

  根据麦角固醇拟议的生物合成方法，由麦角固醇分八步合成了高度氧化的天然产物Chaxine B和BB。关键步骤是使用MCPBA将呋喃中间体氧化成烯醇酯的氧化级联反应，然后进行非对映选择性环氧化和酰氧基迁移。这种简洁的合成方法改变了Chaxine B及其天然类似物的结构，并合成了这些天然产物的非天然类似物用于生物学研究。
• Synthesis of two osteoclast-forming suppressors, demethylincisterol A3 and chaxine A
  作者：Arata Yajima、Yuuma Kagohara、Keisuke Shikai、Ryo Katsuta、Tomoo Nukada

  DOI：10.1016/j.tet.2011.12.057

  日期：2012.2

  The synthesis of two potent osteoclast-forming suppressing agents isolated from the Chinese mushroom Agrocybe chaxingu, demethylincisterol A(3) and chaxine A. was accomplished using ergocalciferol as the starting material. Our methodology for the synthesis of demethylincisterol A(3) and chaxine A featured the construction of a butenolide moiety by the intramolecular Horner-Wadsworth-Emmons reaction under Masamune-Roush conditions. This is the first reported synthesis of chaxine A. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis of (17R)-17-methylincisterol, a highly degraded marine steroid
  作者：Francesco De Riccardis、Aldo Spinella、Irene Izzo、Assunta Giordano、Guido Sodano

  DOI：10.1016/0040-4039(95)00745-x

  日期：1995.6

  The synthesis of (17R)-17-methylincisterol, a highly degraded marine steroid, has been achieved starting from vitamin D-2 in 8 steps and in 13% overall yield. Its O-demethyl analog, which is an intermediate in the synthetic sequence, is possibly the true naturally occurring molecule.
• 4-hydroxy-17-methylincisterol, an inhibitor of DNA polymerase-α activity and the growth of human cancer cells in vitro
  作者：Hideaki Togashi、Yoshiyuki Mizushina、Masaharu Takemura、Fumio Sugawara、Hiroyuki Koshino、Yasuaki Esumi、Jun Uzawa、Hiroyuki Kumagai、Akio Matsukage、Shonen Yoshida、Kengo Sakaguchi

  DOI：10.1016/s0006-2952(98)00197-x

  日期：1998.9

  An ergosterol derivative, 4-hydroxy-17-methylincisterol (HMI), was found to be an inhibitor of mammalian DNA polymerases in vitro. HMI inhibited the activity of calf thymus DNA polymerase alpha (pol. alpha). Among the polymerases tested, pol. alpha was the most sensitive to inhibition by HMI, and the inhibition was concentration dependent. The inhibitory effect of HMI on pol. a was almost the same as that shown by aphidicolin, a well known potent pol. alpha inhibitor. HMI had relatively less effect on rat DNA pol. beta, human immunodeficiency virus type 1 reverse transcriptase (HIV-RT), and calf thymus terminal deoxynucleotidyl transferase (TdT) in vitro, and did not influence the activities of prokaryotic DNA polymerases such as Klenow Fragment of DNA polymerase I, or the DNA-metabolic enzyme DNase I. HMI was found to be able to prevent the growth of human cancer cell lines originating from patients with leukemia or various solid tumors; its IC50 values ranged from 7.5 to 12 mu M. We also synthesized other ergosterol derivatives and tested them, and found that two compounds, 17-methylincisterol and 4-acetyl-17-methylincisterol, have similar inhibitory effects. (C) 1998 Elsevier Science Inc.