1,5-Bis(2-hydroxyphenyl)-pentan-3-ol

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 1,5-Bis(2-hydroxyphenyl)-pentan-3-ol
• 英文别名: 2-[3-Hydroxy-5-(2-hydroxyphenyl)pentyl]phenol
• 化学式: C₁₇H₂₀O₃
• 分子量: 272.344
• InChiKey: AFPCQCKZTYQLRV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (1E,4E)-1,5-bis(2-hydroxyphenyl)penta-1,4-dien-3-one 在 氢气 、 镍 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 1,5-Bis(2-hydroxyphenyl)-pentan-3-ol
  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：——

  公开号：US20020019382A1

  公开（公告）日：2002-02-14

  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.

  本发明涉及表现出抗肿瘤和抗血管生成特性的姜黄素类似物，包括这些化合物的药物配方以及使用这些化合物的方法。
• [EN] CURCUMIN ANALOGUES FOR TREATING CANCER<br/>[FR] ANALOGUES DE CIRCUMINE DESTINES AU TRAITEMENT DU CANCER
  申请人：UNIV EMORY

  公开号：WO2001040188A1

  公开（公告）日：2001-06-07

  The present invention is directed to curcumin analogs (I), wherein Y is OH, halogen, or CF3; Z is H, OH, OR1, halogen, or CF3; X1 and X2 are independently C or N; and A is as defined in the application; exhibiting anti-tumor and anti-angiogenic properties, pharmaceutical formulations including such compounds and methods of using such compounds.

  本发明涉及姜黄素类似物(I)，其中Y为OH、卤素或CF3；Z为H、OH、OR1、卤素或CF3；X1和X2独立地为C或N；A如本申请所定义；该类似物具有抗肿瘤和抗血管生成作用，制备包括这些化合物的制药组合物以及使用这些化合物的方法。
• 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。
• CURCUMIN ANALOGUES FOR TREATING CANCER
  申请人：Emory University

  公开号：EP1242379A1

  公开（公告）日：2002-09-25
• US6664272B2
  申请人：——

  公开号：US6664272B2

  公开（公告）日：2003-12-16