2-(4-hydroxyphenyl)-3-phenyl-7-methoxy-2H-1-benzopyran | 130064-41-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 2-(4-hydroxyphenyl)-3-phenyl-7-methoxy-2H-1-benzopyran
• 英文别名: 4-(7-methoxy-3-phenyl-2H-chromen-2-yl)phenol
• CAS: 130064-41-4
• 化学式: C₂₂H₁₈O₃
• 分子量: 330.383
• InChiKey: HPKHLLZWPBHUOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-hydroxyphenyl)-3-phenyl-7-methoxy-2H-1-benzopyran 、 N-(2-氯乙基)吡咯烷 生成 1-{2-[4-(7-Methoxy-3-phenyl-2H-chromen-2-yl)-phenoxy]-ethyl}-pyrrolidine
  参考文献：
  名称：

  SAEED, A.;SHARMA, A. P.;DURANI, N., J. MED. CHEM., 33,(1990) N2, C. 3210-3216

  摘要：

  DOI：
• 作为产物：
  描述：

  1-(2-羟基-4-甲氧基苯基)-2-苯乙酮 在 哌啶 、 sodium tetrahydroborate 作用下， 以 乙醇 、 苯 为溶剂， 反应 42.0h， 生成 2-(4-hydroxyphenyl)-3-phenyl-7-methoxy-2H-1-benzopyran
  参考文献：
  名称：

  Structure-activity relationship of antiestrogens. Studies on 2,3-diaryl-1-benzopyrans

  摘要：

  A series of 2,3-diaryl-1-benzopyran analogues substituted at position 4 of 2-phenyl with a hydroxy or pyrrolidinoethoxy residue were synthesized as models for (E)-triarylpropenones constrained in the s-trans conformation. The prototypes, belonging to five chemical series, were evaluated for their estrogen receptor affinity and for estrogen agonist-antagonist activities. The 4H-1-benzopyran-4-one, the 2,3-dihydro-4H-1-benzopyran-4-one, the 4H-1-benzopyran, and the 2,3-dihydro-1-benzopyran derivatives were found to be inactive or only marginally activate as receptor ligands or estrogen agonists-antagonists. In the 2H-1-benzopyran category the parent phenol was also inactive whereas the basic ethers 16 and 26 were modest receptor ligands while being quite active as antiestrogens. In a comparative study the benzopyran 16 was found to be more effective antiestrogen than tamoxifen while being as effective as LY-117018. The benzopyrans have thus emerged as a new class of potent antiestrogens.

  DOI：

  10.1021/jm00174a018

文献信息

• [EN] 2-SUBSTITUTED ISOFLAVONOID COMPOUNDS, MEDICAMENTS AND USES<br/>[FR] COMPOSÉS ISOFLAVONOÏDES SUBSTITUÉS EN POSITION 2, MÉDICAMENTS ET UTILISATIONS
  申请人：NOVOGEN RES PTY LTD

  公开号：WO2009003229A1

  公开（公告）日：2009-01-08

  2-Substituted isoflavonoid compounds and pharmaceutical compositions containing same are useful as anti-inflammatory agents and antioxidants and for the treatment of related diseases and conditions.

  2-取代异黄酮化合物和含有这些化合物的药物组合物可用作抗炎剂和抗氧化剂，用于治疗相关疾病和症状。
• 2-SUBSTITUTED ISOFLAVONOID COMPOUNDS, MEDICAMENTS AND USES
  申请人：Eiffe Eleanor

  公开号：US20110166142A1

  公开（公告）日：2011-07-07

  2-Substituted isoflavonoid compounds and pharmaceutical compositions containing same are useful as anti-inflammatory agents and antioxidants and for the treatment of related diseases and conditions.

  2-取代异黄酮化合物及含有其的药物组合物可用作抗炎剂和抗氧化剂，用于治疗相关疾病和症状。
• Structure-activity relationship of antiestrogens. Phenolic analogs of 2,3-diaryl-2H-1-benzopyrans
  作者：Arun P. Sharma、Ashraf Saeed、Susheel Durani、Randhir S. Kapil

  DOI：10.1021/jm00174a020

  日期：1990.12

  Phenolic analogues of 2-[4-(2-piperidinoethoxy)phenyl]-3-phenyl-2H-1-benzopyran (1), a novel antiestrogen, were synthesized and evaluated for their structure-activity relationship. Incorporation of OH at position 7 was found to improve receptor affinity of the benzopyran while having no effect on its action as an antagonist. Similar substitution of 2-phenyl as well potentiated receptor affinity as well as antagonist activity of the prototype. The monophenol 19 and the diphenol 25 were thus found to be good receptor ligands, devoid of estrogen agonist activity and associated with marked antiestrogenic activity of comparable order. Both caused nearly complete inhibition of the estradiol stimulated uterine growth in rats as well as mice and were thus found to be better antiestrogens than tamoxifen, trioxifen, and LY-117018. A binding-site model for estrogen receptor rationalizing the structure-activity relationship of benzopyrans in relation to that of the triarylethylene and the triarylpropenone antiestrogens has been discussed.
• SAEED, A.;SHARMA, A. P.;DURANI, N., J. MED. CHEM., 33,(1990) N2, C. 3210-3216
  作者：SAEED, A.、SHARMA, A. P.、DURANI, N.

  DOI：——

  日期：——
• US5254568A
  申请人：——

  公开号：US5254568A

  公开（公告）日：1993-10-19