3-acetoxy-4-chloro-6-formyl-5-methyl-2-[(2E,4E)-3-methyl-5-((1R,2R,6R)-1,2,6-trimethyl-3-oxocyclohexyl)-2,4-pentadienyl]phenyl acetate | 462125-47-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 3-acetoxy-4-chloro-6-formyl-5-methyl-2-[(2E,4E)-3-methyl-5-((1R,2R,6R)-1,2,6-trimethyl-3-oxocyclohexyl)-2,4-pentadienyl]phenyl acetate
• 英文别名: 2,4-di-O-acetylascochlorin；2,4-di-O-ascochlorin；diacetylascochlorin；[5-acetyloxy-4-chloro-2-formyl-3-methyl-6-[(2E,4E)-3-methyl-5-[(1R,2R,6R)-1,2,6-trimethyl-3-oxocyclohexyl]penta-2,4-dienyl]phenyl] acetate
• CAS: 462125-47-9
• 化学式: C₂₇H₃₃ClO₆
• 分子量: 489.008
• InChiKey: ZAZPZYCLNRIXNL-XHQJDYTKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  86.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-acetoxy-4-chloro-6-formyl-5-methyl-2-[(2E,4E)-3-methyl-5-((1R,2R,6R)-1,2,6-trimethyl-3-oxocyclohexyl)-2,4-pentadienyl]phenyl acetate 在 水 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 4-O-Acetylascochlorin
  参考文献：
  名称：

  NOVEL TRANSCRIPTIONAL FACTOR, PROCESS FOR PRODUCING THE SAME AND USE THEREOF

  摘要：

  公开号：

  EP1616856B1
• 作为产物：
  描述：

  壳二孢氯素 、 乙酰氯 在 吡啶 作用下， 反应 4.0h， 以88%的产率得到3-acetoxy-4-chloro-6-formyl-5-methyl-2-[(2E,4E)-3-methyl-5-((1R,2R,6R)-1,2,6-trimethyl-3-oxocyclohexyl)-2,4-pentadienyl]phenyl acetate
  参考文献：
  名称：

  Method for preparing novel transcription factors and use

  摘要：

  本发明的目的是开发新的化合物，用于治疗综合征X、癌症、黏液水肿、血管慢性炎症等疾病，并且预防/治疗由气球或支架扩张引起的动脉再狭窄，通过抑制自体细胞或组织的排斥反应促进再生医学，并提供制备这些化合物的方法。发现通过对ascochlorin及其类似物中2-位置的羟基进行酰化，并在碱性催化剂存在下将醇键合到醛基上，可以实现这一目标，从而获得新的缩醛衍生物。

  公开号：

  US20070054966A1

文献信息

• Process for preparing transcription factors and their use
  申请人：NRL Pharma, Inc.

  公开号：EP1762558A1

  公开（公告）日：2007-03-14

  The present invention has an object to develop novel compounds which are effective for the therapy of syndrome X, cancer, myxedema, vascular chronic inflammation and the like, and furthermore prevent/treat the restenosis caused in an artery expansion by a balloon or a stent and have the activity facilitating regenerative medicine by inhibiting rejection of own cells or tissues to be transplanted and the method for preparing the same. Novel acetal derivatives obtained by acylating the hydroxyl group at the 2-position of the orcylaldehyde which ascochlorin and its analogs have and thereafter bonding an alcohol to the aldehyde group in the presence of a basic catalyst are found to achieve the object.

  本发明的目的是开发新的化合物，用于治疗综合征X、癌症、黏液水肿、血管慢性炎症等疾病，并能够预防/治疗由气球或支架扩张引起的动脉再狭窄，并通过抑制自体细胞或组织的排斥作用促进再生医学的活性，以及其制备方法。通过在基本催化剂的存在下，酰化ascochlorin及其类似物具有的orcylaldehyde的2位羟基，并在醛基上结合醇，得到新的缩醛衍生物，发现可以实现该目的。
• Ascochlorin Derivatives as Ligands for Nuclear Hormone Receptors
  作者：Marie Togashi、Satoshi Ozawa、Shoko Abe、Tomoyuki Nishimura、Mie Tsuruga、Kunio Ando、Gakuzo Tamura、Shigefumi Kuwahara、Makoto Ubukata、Junji Magae

  DOI：10.1021/jm0205649

  日期：2003.9.1

  Nuclear receptor family proteins are structurally related transcription factors activated by specific lipophilic compounds. Because they are activated by a variety of hormonal molecules, including retinoic acid, vitamin D, and steroid hormones, they are assumed to be promising targets for clinical drugs. We previously found that one ascochlorin (1) derivative, 4-O-carboxymethyl-ascochlorin (2), is a potent agonist of peroxisome proliferator activated receptor gamma (PPARgamma). Here, we synthesized derivatives of 1, designated as a lead compound, to create new modulators of nuclear hormone receptors. Two derivatives, 4-O-carboxymethyl-2-O-methylascochlorin (9) and 4-O-isonicotinoyl-2-O-methylasco(hlorin (10), showed improved agonistic activity for PPARgamma and induced differentiation of a progenitor cell line, C3HIOT1/2. We also found that 1, dehydroascofuranon (29), and a 2,4-0-diacetyl-1-carboxylic acid derivative of 1 (5) specifically activated estrogen receptors, PPARalpha, and an androgen receptor. All of the derivatives (1-29) activated the pregnane X receptor. These results suggest that the chemical structure of 1 is useful in designing novel modulators of nuclear receptors.
• EP1481670
  申请人：——

  公开号：——

  公开（公告）日：——
• US7432306B2
  申请人：——

  公开号：US7432306B2

  公开（公告）日：2008-10-07
• US7629471B2
  申请人：——

  公开号：US7629471B2

  公开（公告）日：2009-12-08