1t,5t-bis-(2-acetoxy-phenyl)-penta-1,4-dien-3-one | 126794-38-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 1t,5t-bis-(2-acetoxy-phenyl)-penta-1,4-dien-3-one
• 英文别名: 1,5-bis-(2-acetoxy-phenyl)-penta-1,4-dien-3-one；1t,5t-Bis-(2-acetoxy-phenyl)-penta-1,4-dien-3-on；1,5-Bis-(2-acetoxy-phenyl)-penta-1,4-dien-3-on；2-(5-(2-(Acetyloxy)phenyl)-3-oxo-1,4-pentadienyl)phenyl acetate；[2-[(1E,4E)-5-(2-acetyloxyphenyl)-3-oxopenta-1,4-dienyl]phenyl] acetate
• CAS: 126794-38-5
• 化学式: C₂₁H₁₈O₅
• 分子量: 350.371
• InChiKey: RNHOOXNUFNRJSM-PHEQNACWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1t,5t-bis-(2-acetoxy-phenyl)-penta-1,4-dien-3-one 、 2-[Bromo(dimethyl)-lambda4-sulfanyl]-1-(4-chlorophenyl)ethanone 、 sodium hydroxide 、 水 、 苄基三乙基氯化铵 以76%的产率得到
  参考文献：
  名称：

  SARADA, S.;, REDDY G. RAMACHANDRA, SULFUR LETT., 10,(1989) N-4, C. 143-148

  摘要：

  DOI：
• 作为产物：
  描述：

  (1E,4E)-1,5-bis(2-hydroxyphenyl)penta-1,4-dien-3-one 、 乙酰氯 在 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 以80%的产率得到1t,5t-bis-(2-acetoxy-phenyl)-penta-1,4-dien-3-one
  参考文献：
  名称：

  Synthesis and biological evaluation of novel curcumin analogs as anti-cancer and anti-angiogenesis agents

  摘要：

  A series of novel curcumin analogs were synthesized and screened for anti-cancer and anti-angiogenesis activities at Emory University and at the National Cancer Institute (NCI). These compounds are symmetrical alpha,beta-unsaturated and saturated ketones. The majority of the analogs demonstrated a moderate degree of anti-cancer activity. Compounds 10, 11, and 14 exhibited a high degree of cytotoxicity in the NCI in vitro anti-cancer cell line screen. In addition, this screen revealed that these compounds inhibit tumor cell growth with a higher potency than the commonly used chemotherapeutic drug, cisplatin. In independent in vitro screens conducted at Emory, the same compounds plus 4, 5, 8, 9, and 13 exhibited a high degree of cytotoxicity to tumor cells. Analogs that were effective in the anti-cancer screens were also effective in in vitro anti-angiogenesis assays. Compounds 4, 9, 11, and 14 were most effective in the anti-angiogenesis assays run at Emory. In the assays conducted by the NCI, compound 14 was almost as potent as the anti-angiogenic drug TNP-470, which has undergone clinical trials. Based on the favorable in vitro anti-cancer and anti-angiogenesis results with 14, further in vivo tests were conducted. This compound effectively reduced the size of human breast tumors grown in female athymic nude mice and showed little toxicity. This data, coupled with the remarkable in vitro data, suggests that compound 14 may potentially be an effective chemotherapeutic agent. As a follow-up, a 3D quantitative structure relationship based on 14 has been developed. It shows a cross-validated r(2)(q(2)) = 0.83 and a predictive r(2)(p(2)) = 0.71. COMPARE analysis suggests the compound to be a possible RNA/DNA antimetabolite, but also implies that the compound's cytotoxicity may arise from a presently unknown mechanism. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.05.006

文献信息

• CURCUMIN ANALOGS WITH ANTI-TUMOR AND ANTI-ANGIOGENIC PROPERTIES
  申请人：Snyder James P.

  公开号：US20080234320A1

  公开（公告）日：2008-09-25

  The present invention is directed to curcumin analogs exhibiting anti-tumor and anti-angiogenic properties, pharmaceutical formulations including such compounds and methods of using such compounds.

  本发明涉及展现抗肿瘤和抗血管生成特性的姜黄素类似物，包括这些化合物的制药配方和使用这些化合物的方法。
• On Disalicylideneacetone and Analogs
  作者：Peter T. Mora、Tibor Széki

  DOI：10.1021/ja01163a059

  日期：1950.7
• SARADA, S.;, REDDY G. RAMACHANDRA, SULFUR LETT., 10,(1989) N-4, C. 143-148
  作者：SARADA, S.、, REDDY G. RAMACHANDRA

  DOI：——

  日期：——
• US7371766B2
  申请人：——

  公开号：US7371766B2

  公开（公告）日：2008-05-13
• US7842705B2
  申请人：——

  公开号：US7842705B2

  公开（公告）日：2010-11-30