6-hydroxy-2,3-diphenyl-indole | 29952-48-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 6-hydroxy-2,3-diphenyl-indole
• 英文别名: 2,3-diphenyl-indol-6-ol；6-Hydroxy-2,3-diphenyl-1H-indole；2,3-Diphenyl-1H-indol-6-ol；2,3-Diphenyl-6-hydroxy-indol；6-Hydroxy-2,3-diphenyl-indol
• CAS: 29952-48-5
• 化学式: C₂₀H₁₅NO
• 分子量: 285.345
• InChiKey: YTHSDENFEODFME-UHFFFAOYSA-N

物化性质

• 熔点：
  168 °C
• 沸点：
  504.4±38.0 °C(Predicted)
• 密度：
  1.235±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  36
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6-hydroxy-2,3-diphenyl-indole 在 potassium dihydrogenphosphate 、 potassium nitrososulfonate 、 丙酮 作用下， 生成 2,3-diphenyl-indole-6,7-dione
  参考文献：
  名称：

  Clifford et al., Journal of the Chemical Society, 1961, p. 3516,3518

  摘要：

  DOI：
• 作为产物：
  描述：

  间苯胺氢氟乙酰氯 在 三氯化铝 、 苯 作用下， 生成 6-hydroxy-2,3-diphenyl-indole
  参考文献：
  名称：

  Teuber; Schnee, Chemische Berichte, 1958, vol. 91, p. 2089,2093

  摘要：

  DOI：

文献信息

• Mechanochemical synthesis of coumarins <i>via</i> Pechmann condensation under solvent-free conditions: an easy access to coumarins and annulated pyrano[2,3-<i>f</i>] and [3,2-<i>f</i>]indoles
  作者：Ainur D. Sharapov、Ramil F. Fatykhov、Igor A. Khalymbadzha、Vladimir V. Sharutin、Sougata Santra、Grigory V. Zyryanov、Oleg N. Chupakhin、Brindaban C. Ranu

  DOI：10.1039/d1gc04564d

  日期：——

  A green protocol has been developed for the synthesis of simple coumarins and linear pyrano[2,3-f] and [3,2-f]indoles by the reaction of phenol derivatives with β-ketoesters under ball milling at ambient temperature in the presence of methanesulfonic acid as a mild acid catalyst. The significant advantages of this procedure are high yields, scalability, no use of hazardous acids or solvents, shorter

  已开发出一种绿色方案，用于通过苯酚衍生物与 β-酮酯在环境温度下球磨下的反应，合成简单的香豆素和线性吡喃并[2,3- f ] 和 [3,2 - f ] 吲哚。甲磺酸作为温和的酸催化剂。该方法的显着优势是高产率、可扩展性、不使用有害酸或溶剂、反应时间短、环境温度低、成本低以及无需柱色谱即可直接纯化。此过程与高 EcoScale 指标和低E因子相关联。与传统的 Pechmann 缩合过程相比，机械化学方案可合成具有优异区域选择性和高产率的吡喃吲哚。
• Novel bicyclic compounds
  申请人：——

  公开号：US20030191174A1

  公开（公告）日：2003-10-09

  Compounds of the general formula (I): 1 or a salt thereof, wherein R 1 is hydrogen, hydroxyl or halogen; R 2 is NHSO 2 CH 3 , SO 2 NHCH 3 or the like; R 5 and R 6 each independently is hydrogen, C 1-6 alkyl, optionally substituted phenyl or optionally substituted benzyl; X is NH, sulfur, oxygen or methylene; Y is oxygen, NR 7 , sulfur, methylene or a bond; and * represents an asymmetric carbon atom. The compounds are useful as a medicine for treating or preventing diabetes, obesity, hyperlipidemia, digestive diseases, depression or urinary disturbances.

  通式（I）的化合物：1或其盐，其中R1是氢、羟基或卤素；R2是NHSO2CH3、SO2NHCH3或类似物；R5和R6各自独立地是氢、C1-6烷基、可选择取代的苯基或可选择取代的苄基；X是NH、硫、氧或亚甲基；Y是氧、NR7、硫、亚甲基或键；*代表一个不对称的碳原子。这些化合物可用作治疗或预防糖尿病、肥胖症、高脂血症、消化系统疾病、抑郁症或尿路紊乱的药物。
• Synthesis and Estrogen Receptor Affinity of 2,3-Diarylindoles
  作者：Josef Strohmeier、Erwin Von Angerer

  DOI：10.1002/ardp.19873200506

  日期：——

  the aromatic rings were synthesized and tested for their binding affinity for the calf uterine estrogen receptor. Most of these indoles bind to the estrogen receptor. The highest binding affinity (1,25 % of estradiol) was found with 3‐(4‐hydroxyphenyl)‐2‐phenylindole (3b). The acetate of 3b was studied in vivo. It was devoid of estrogenic or antiestrogenic activity in the mouse and inhibited only weakly

  合成了在 C-3 处具有芳香取代基和在芳香环处具有羟基官能团的 2-苯基吲哚，并测试了它们对小牛子宫雌激素受体的结合亲和力。大多数这些吲哚与雌激素受体结合。3-(4-羟基苯基)-2-苯基吲哚 (3b) 的结合亲和力最高（雌二醇的 1.25%）。体内研究了3b的乙酸盐。它在小鼠体内没有雌激素或抗雌激素活性，并且仅微弱地抑制了激素依赖性 DMBA 诱导的大鼠乳腺肿瘤的生长。
• Indole compounds and their use as estrogen agonists/antagonists
  申请人：——

  公开号：US20030220377A1

  公开（公告）日：2003-11-27

  This invention relates to compounds, in particular indoles, that are useful as estrogen agonists and antagonists and pharmaceutical uses thereof. The present invention also relates to indoles that are selective for the ER&bgr; receptor and pharmaceutical uses thereof. The compounds have utility in that they may be used to treat estrogen mediated disorders.

  该发明涉及一种化合物，特别是吲哚类化合物，可用作雌激素激动剂和拮抗剂，以及其药用用途。本发明还涉及对ER&bgr;受体具有选择性的吲哚类化合物及其药用用途。这些化合物具有实用价值，因为它们可以用于治疗雌激素介导的疾病。
• NOVEL BICYCLIC COMPOUNDS
  申请人：Asahi Kasei Kabushiki Kaisha

  公开号：EP1277736A1

  公开（公告）日：2003-01-22

  Compounds of the general formula (I): or a salt thereof, wherein R1 is hydrogen, hydroxyl or halogen; R2 is NHSO2CH3, SO2NHCH3 or the like; R5 and R6 each independently is hydrogen, C1-6 alkyl, optionally substituted phenyl or optionally substituted benzyl; X is NH, sulfur, oxygen or methylene; Y is oxygen, NR7, sulfur, methylene or a bond; and * represents an asymmetric carbon atom. The compounds are useful as a medicine for treating or preventing diabetes, obesity, hyperlipidemia, digestive diseases, depression or urinary disturbances.

  通式（I）的化合物： 或其盐，其中 R1 是氢、羟基或卤素；R2 是 NHSO2CH3、SO2NHCH3 或类似物；R5 和 R6 各自独立地是氢、C1-6 烷基、任选取代的苯基或任选取代的苄基；X 是 NH、硫、氧或亚甲基；Y 是氧、NR7、硫、亚甲基或键；* 代表不对称碳原子。 这些化合物可用作治疗或预防糖尿病、肥胖症、高脂血症、消化系统疾病、抑郁症或泌尿系统紊乱的药物。