Myricerone | 145039-10-7

• 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: Myricerone
• 英文别名: (4aS,6aR,6aR,6bR,8aR,12aR,14bS)-6a-(hydroxymethyl)-2,2,6b,9,9,12a-hexamethyl-10-oxo-3,4,5,6,6a,7,8,8a,11,12,13,14b-dodecahydro-1H-picene-4a-carboxylic acid
• CAS: 145039-10-7
• 化学式: C₃₀H₄₆O₄
• 分子量: 470.693
• InChiKey: WVGVTIMZQLYBLX-SXOOSYOQSA-N

物化性质

• 沸点：
  590.3±50.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  34
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Myricerone 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N'-羰基二咪唑 、 三氟乙酸 、 lithium chloride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.5h， 生成 (4-碘-苯甲基)-膦酸二乙基酯
  参考文献：
  名称：

  Practical Partial Synthesis of Myriceric Acid A, an Endothelin Receptor Antagonist, from Oleanolic Acid

  摘要：

  Myriceric acid A (1) is an oleanane triterpene that is a potent and specific endothelin A receptor antagonist. A practical procedure for large-scale synthesis of myriceric acid A (1) has been developed starting from oleanolic acid 4. The conversion of oleanolic acid 4 to the key intermediate myricerone 3 was achieved in an efficient manner employing a photochemical reaction (the Barton reaction) of nitrite 7. Our synthetic procedure alleviated several difficulties of the original Barton's procedure with regard to yields and large-scale operation. Myricerone 3 afforded Horner-Wadsworth-Emmons (HWE) type phosphonate 2 which has proved to be a versatile precursor of 1. The preparation of phosphonate 2 on a scale of several hundred grams is described. The synthesis was completed by condensation of 2 with 3,4-bis[(diphenylmethyl)oxy]benzaldehyde (21), giving alpha,beta-unsaturated ester 22, which was deprotected to afford 1. The whole synthetic sequence is efficient (14 steps, 31% yield) and requires no chromatographic purification except to obtain the final product 1.

  DOI：

  10.1021/jo9615864
• 作为产物：
  描述：

  (4-碘-苯甲基)-膦酸二乙基酯 在 氢氧化钾 作用下， 反应 3.0h， 以4.8 mg的产率得到Myricerone
  参考文献：
  名称：

  Endothelin Receptor Antagonist Triterpenoid, Myriceric Acid A, Isolated from Myrica cerifera, and Structure Activity Relationships of Its Derivatives.

  摘要：

  作为第一种非肽类内皮素受体拮抗剂，新的三萜类化合物——美洲杜鹃酸A（myiceric acid A，50-235）（1）是从海梅果（Myrica cerifera）中分离得到的。美洲杜鹃酸A（1）不仅抑制了内皮素-1诱导的细胞质游离Ca<2+>浓度的增加（IC50 = 11±2 nM），还抑制了[<125&I]内皮素-1在大鼠主动脉平滑肌细胞中的结合（Ki = 66±15 nM）。此外，还分离出了两种新的相关三萜类化合物，美洲杜鹃酸C（6）和美洲杜鹃酸D（8）。进一步地，对这些天然产物的化学修饰导致合成了硫酸酯衍生物（13、14、15），其对内皮素受体的亲和力提高了1.5到20倍。讨论了美洲杜鹃酸及其衍生物的结构活性关系。

  DOI：

  10.1248/cpb.44.343

文献信息

• Synthesis and Evaluation of Several 3,4-Seco-Derivatives of Myricerone as Endothelin Receptor Antagonists
  作者：Junyi Hu、Chengfei Liu、Yingqian Xu、Yun Gao、Guoyong Xiao

  DOI：10.1007/s10600-014-0989-6

  日期：2014.7

  3,4-Seco-derivatives of myricerone were prepared by the Baeyer–Villiger oxidation of myricerone, and their structures were elucidated based on NMR and MS analyses. The synthesized compounds were evaluated as endothelin receptor antagonists and exhibited significant binding affinity for the ETA receptor.

  通过Baeyer-Villiger氧化法对杨梅酮进行氧化，制备了杨梅酮的3,4-seco-衍生物，并通过核磁共振和质谱分析阐明了其结构。经评估，合成的化合物是内皮素受体拮抗剂，对ETA受体表现出显著的亲和力。
• EP1757573
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis of [2-13C]-oleanolic acid and [2-13C]-myricerone
  作者：Toshiro Konoike、Kazuhiro Takahashi、Yoji Kitaura、Yasuhiko Kanda

  DOI：10.1016/s0040-4020(99)00975-8

  日期：1999.12

  Synthetic way for C-13-labeled oleanolic acid I and myricerone 2 has been developed, starting from the parent 1 and 2. The procedure involves ring opening and closure of the A rings of these oleanane triterpenes. C-13 was introduced into the 2-position by C-13-MeLi as an isotope source. Chelation controlled addition of methyllithium to alpha-hydoxypentanone 11 is a common crucial step for labeling of 1 and 2, and judicious choice of protecting groups is essential for 2. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Practical Large-Scale Synthesis of Endothelin Receptor Antagonist S-0139
  作者：Toshiro Konoike、Katsuo Oda、Masaaki Uenaka、Kazuhiro Takahashi

  DOI：10.1021/op990036f

  日期：1999.9.1
• US7645793B2
  申请人：——

  公开号：US7645793B2

  公开（公告）日：2010-01-12