5-hydroxy-4,7-dimethylindan | 28567-20-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 5-hydroxy-4,7-dimethylindan
• 英文别名: 4,7-Dimethyl-indan-5-ol；4,7-Dimethyl-5-hydorxyindane；4,7-dimethyl-2,3-dihydro-1H-inden-5-ol
• CAS: 28567-20-6
• 化学式: C₁₁H₁₄O
• 分子量: 162.232
• InChiKey: ZITTVZXGTMFMSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-hydroxy-4,7-dimethylindan 在 Celite 、 三氟化硼乙醚 、 pyridinium chlorochromate 作用下， 以 1,2-二氯乙烷 、 苯 为溶剂， 反应 8.0h， 生成 7-(4-Fluoro-phenyl)-7-(6-hydroxy-4,7-dimethyl-3-oxo-indan-5-yl)-heptanoic acid methyl ester
  参考文献：
  名称：

  Synthesis and thromboxane A2/prostaglandin H2 receptor antagonistic activity of phenol derivatives

  摘要：

  Consideration of possible structural similarities between thromboxane A2 and the hydroquinone form of (R)-(+)-7-(3,5,6-trimethyl-1,4-benzoquinon-2-yl)-7-phenylheptanoic acid (R-(+)-AA-2414) led to the development of a new series of thromboxane A2/prostaglandin H-2 (TXA2/PGH2) receptor antagonists, namely 7-(4-fluorophenyl)-7-(2-hydroxyphenyl)heptanoic acids (I). These compounds were found to be potent TXA2/PGH2 receptor antagonists. Compounds having either a carbonyl or a hydroxymethyl group at the para-position of the phenolic hydroxy group exhibited most potent activities in this series. Compounds 14, 15, 18, and 26 inhibited the specific binding of [H-3]U-46619 to guinea pig platelet membranes (IC50 = 4.4, 80, 32, and 13 nM, respectively), and also inhibited U-46619-induced human platelet aggregation (IC50 = 310, 69, 79, and 78 nM, respectively). Comparison of the UV spectra of the compounds with a carbonyl group at the para-position of phenolic hydroxy group revealed that the activity tended to increase in accordance with a decrease in the torsional angle between the carbonyl group and the phenol ring. These results suggested that the spacial location of the carbonyl and hydroxymethyl oxygen are important for significant increase in activity and that the carbonyl and hydroxymethyl oxygen at the para-position of the phenolic hydroxy group might interact with one of the TXA2/PGH2 receptor sites.

  DOI：

  10.1021/jm00090a009
• 作为产物：
  描述：

  6-methoxy-4,7-dimethyl-1-indanone 在 钯 sodium tetrahydroborate 、 氢气 、 三溴化硼 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 5.0h， 生成 5-hydroxy-4,7-dimethylindan
  参考文献：
  名称：

  Synthesis and thromboxane A2/prostaglandin H2 receptor antagonistic activity of phenol derivatives

  摘要：

  Consideration of possible structural similarities between thromboxane A2 and the hydroquinone form of (R)-(+)-7-(3,5,6-trimethyl-1,4-benzoquinon-2-yl)-7-phenylheptanoic acid (R-(+)-AA-2414) led to the development of a new series of thromboxane A2/prostaglandin H-2 (TXA2/PGH2) receptor antagonists, namely 7-(4-fluorophenyl)-7-(2-hydroxyphenyl)heptanoic acids (I). These compounds were found to be potent TXA2/PGH2 receptor antagonists. Compounds having either a carbonyl or a hydroxymethyl group at the para-position of the phenolic hydroxy group exhibited most potent activities in this series. Compounds 14, 15, 18, and 26 inhibited the specific binding of [H-3]U-46619 to guinea pig platelet membranes (IC50 = 4.4, 80, 32, and 13 nM, respectively), and also inhibited U-46619-induced human platelet aggregation (IC50 = 310, 69, 79, and 78 nM, respectively). Comparison of the UV spectra of the compounds with a carbonyl group at the para-position of phenolic hydroxy group revealed that the activity tended to increase in accordance with a decrease in the torsional angle between the carbonyl group and the phenol ring. These results suggested that the spacial location of the carbonyl and hydroxymethyl oxygen are important for significant increase in activity and that the carbonyl and hydroxymethyl oxygen at the para-position of the phenolic hydroxy group might interact with one of the TXA2/PGH2 receptor sites.

  DOI：

  10.1021/jm00090a009

文献信息

• Stereoselective Synthesis and Thromboxane A2 (TXA2) Receptor Antagonistic Activity of Optically Active Phenol Derivatives.
  作者：Shoji FUKUMOTO、Zen-ichi TERASHITA、Yasuko ASHIDA、Shinji TERAO、Mitsuru SHIRAISHI

  DOI：10.1248/cpb.44.749

  日期：——

  Enantiomers of four potent nonprostanoid thromboxane A2 (TXA2) receptor antagonists, (+/-)-7-(4-fluorophenyl)-7-(2-hydroxyphenyl)heptanoic acids (1-4), were synthesized stereoselectively by direct ortho-alkylation of phenols under modified Mitsunobu conditions. The reaction of 5 eq of phenols (6a-c) with 1 eq of (S)- or (R)-methyl 7-(4-fluorophenyl)-7-hydroxyheptanoate ((S)- or (R)-7) afforded ortho-alkylated

  四种有效的非前列腺素血栓烷A2（TXA2）受体拮抗剂的对映体（+/-）-7-（4-氟苯基）-7-（2-羟苯基）庚酸（1-4）是通过直接邻位烷基化立体选择性合成的在改良的Mitsunobu条件下制备苯酚。5eq的酚（6a-c）与1eq的（S）-或（R）-甲基7-（4-氟苯基）-7-羟基庚酸酯（（S）-或（R）-7）反应，得到对映选择性的对烷基烷基苯酚衍生物（6a-c），化学产率为33％至42％，ee为90％至93％。在这些化合物中，（R）-对映体（1-4）表现出有效的TXA2受体拮抗活性，而（S）-异构体（3）的活性低得多。特别是，化合物（R）-3强烈抑制U-46619诱导的人血小板聚集（IC50 = 48 nM），并且还显示出非常有效的抑制作用，最低有效剂量（MED）为0.3 mg / kg（po
• Phenol derivatives, their production and use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US05162571A1

  公开（公告）日：1992-11-10

  Novel phenol derivatives of the general formula: ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, X, Y and n are as defined in the specification, which have therapeutic and prophylactic activities against cerebral, cardiac, renal and pulmonary circulatory system diseases, respiratory diseases, allergy, anaphylactic shock, endotoxin shock, inflammation and the like as well as inhibiting activities against vascularization by oncocytes.

  一种新的苯酚衍生物，其通式为：##STR1## 其中R.sup.1，R.sup.2，R.sup.3，R.sup.4，R.sup.5，X，Y和n如规范中所定义，具有治疗和预防脑、心、肾和肺循环系统疾病、呼吸系统疾病、过敏、过敏性休克、内毒素休克、炎症等方面的治疗和预防作用，以及对肿瘤细胞血管化的抑制作用。
• An Investigation of the Mills-Nixon Effect
  作者：Louis F. Fieser、Warren C. Lothrop

  DOI：10.1021/ja01301a066

  日期：1936.10
• Nilsson,J.L.G. et al., Acta Chemica Scandinavica (1947), 1970, vol. 24, # 2, p. 580 - 588
  作者：Nilsson,J.L.G. et al.

  DOI：——

  日期：——
• Further Evidence on the Mills-Nixon Effect
  作者：Warren C. Lothrop

  DOI：10.1021/ja01858a035

  日期：1940.1