5-(3,5-dimethylphenyl)-2,3-dihydro-1H-inden-1-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 5-(3,5-dimethylphenyl)-2,3-dihydro-1H-inden-1-one
• 英文别名: 5-(3,5-dimethylphenyl)-2,3-dihydroinden-1-one
• 化学式: C₁₇H₁₆O
• 分子量: 236.313
• InChiKey: GIUFYOZWBXQWOA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-(3,5-dimethylphenyl)-2,3-dihydro-1H-inden-1-one 、 硫脲 在 碘 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以84%的产率得到6-(3,5-dimethylphenyl)-4H-indeno[1,2-d][1,3]thiazol-1-ium-2-amine;iodide
  参考文献：
  名称：

  6-Aryl-8H-indeno[1,2-d]thiazol-2-ylamines:  A₁ Adenosine Receptor Agonist Allosteric Enhancers Having Improved Potency

  摘要：

  Allosteric enhancers (AEs) of the A(1) adenosine receptor (A(1)AR) have potential as drugs for treating neurological, cardiovascular, and renal diseases. This report describes the synthesis and evaluation of a series of 6-aryl-8H-indeno[1,2-d]thiazol-2-ylamines that exhibited AE activity at the A(1)AR. Palladium-mediated condensation of arylboronic acids with 5-bromoindan-1-one generated arylindanones 2a-aj for iodine-catalyzed condensation with thiourea, generating 2-aminothiazolium salts 3a-aj. Binding studies using membranes from cells stably expressing human A(1)ARs, A(2A)ARs, or A(3)ARs evaluated AE activity and receptor subtype selectivity. The EC50 of the AE activities of compounds 3m-o, 3x, and 3ae were 2.2, 1.5, 0.9, 1.0, and 3.0,mu M, respectively, substantially lower than that of the well characterized 2-amino3-aroylthiophene (PD 81,723), > 10 mu M. The new compounds also have substantially higher maximal AE activity. These compounds had no AE activity at the A(2A)AR and only minimal activity at the A(3)AR.

  DOI：

  10.1021/jm049132j
• 作为产物：
  描述：

  4-甲氧基-3,5-二甲基苯硼酸 在 bis-triphenylphosphine-palladium(II) chloride 、 三氟二甲基硫醚络合物 、 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 20.0~85.0 ℃ 、206.85 kPa 条件下， 反应 9.0h， 生成 5-(3,5-dimethylphenyl)-2,3-dihydro-1H-inden-1-one
  参考文献：
  名称：

  [EN] NOVEL COMPOUNDS WHICH ACTIVATE ESTROGEN RECEPTORS AND COMPOSITIONS AND METHODS OF USING THE SAME
  [FR] NOUVEAUX COMPOSÉS QUI ACTIVENT LES RÉCEPTEURS D'ŒSTROGÈNE ET COMPOSITIONS ET PROCÉDÉS D'UTILISATION DE CEUX-CI

  摘要：

  提供了本处所提供的化合物的化学式。这些化合物可能包括具有组织选择性活性的途径优先雌激素（PaPEs）衍生物。此外，还提供了包含这些化合物的药物组合物，以及治疗疾病或症状的方法，包括给予这些化合物。这种疾病或症状可能包括绝经后症状、心血管疾病、中风、血管疾病、骨疾病、代谢疾病、关节炎、骨质疏松症、肥胖、血管运动/潮热、认知能力下降、癌症包括乳腺癌。

  公开号：

  WO2017120507A1

文献信息

• Compounds which activate estrogen receptors and compositions and methods of using the same
  申请人：The Board of Trustees of the University of Illinois

  公开号：US10703698B2

  公开（公告）日：2020-07-07

  Provided are compounds of formulae provided herein. The compounds may include pathway-preferential estrogens (PaPEs) derivatives with tissue-selective activities. Also provided are pharmaceutical compositions comprising the compounds, as well as methods of treating a disease or condition including administering the compounds. The disease or condition may include postmenopausal symptoms, cardiovascular disease, stroke, vascular disease, bone disease, metabolic disease, arthritis, osteoporosis, obesity, vasomotor/hot flush, cognitive decline, cancer including breast cancer.

  本文提供的是式化合物。这些化合物可包括具有组织选择活性的途径优选雌激素（PaPEs）衍生物。还提供了包含这些化合物的药物组合物，以及包括施用这些化合物在内的治疗疾病或病症的方法。疾病或病症可包括绝经后症状、心血管疾病、中风、血管疾病、骨病、代谢疾病、关节炎、骨质疏松症、肥胖症、血管运动/发热、认知能力下降、癌症（包括乳腺癌）。
• NOVEL COMPOUNDS WHICH ACTIVATE ESTROGEN RECEPTORS AND COMPOSITIONS AND METHODS OF USING THE SAME
  申请人：The Board of Trustees of the University of Illinois

  公开号：EP3400071A1

  公开（公告）日：2018-11-14
• 6-Aryl-8<i>H</i>-indeno[1,2-<i>d</i>]thiazol-2-ylamines:  A₁ Adenosine Receptor Agonist Allosteric Enhancers Having Improved Potency
  作者：Mahendra D. Chordia、Molly Zigler、Lauren J. Murphree、Heidi Figler、Timothy L. Macdonald、Ray A. Olsson、Joel Linden

  DOI：10.1021/jm049132j

  日期：2005.8.1

  Allosteric enhancers (AEs) of the A(1) adenosine receptor (A(1)AR) have potential as drugs for treating neurological, cardiovascular, and renal diseases. This report describes the synthesis and evaluation of a series of 6-aryl-8H-indeno[1,2-d]thiazol-2-ylamines that exhibited AE activity at the A(1)AR. Palladium-mediated condensation of arylboronic acids with 5-bromoindan-1-one generated arylindanones 2a-aj for iodine-catalyzed condensation with thiourea, generating 2-aminothiazolium salts 3a-aj. Binding studies using membranes from cells stably expressing human A(1)ARs, A(2A)ARs, or A(3)ARs evaluated AE activity and receptor subtype selectivity. The EC50 of the AE activities of compounds 3m-o, 3x, and 3ae were 2.2, 1.5, 0.9, 1.0, and 3.0,mu M, respectively, substantially lower than that of the well characterized 2-amino3-aroylthiophene (PD 81,723), > 10 mu M. The new compounds also have substantially higher maximal AE activity. These compounds had no AE activity at the A(2A)AR and only minimal activity at the A(3)AR.
• [EN] NOVEL COMPOUNDS WHICH ACTIVATE ESTROGEN RECEPTORS AND COMPOSITIONS AND METHODS OF USING THE SAME<br/>[FR] NOUVEAUX COMPOSÉS QUI ACTIVENT LES RÉCEPTEURS D'ŒSTROGÈNE ET COMPOSITIONS ET PROCÉDÉS D'UTILISATION DE CEUX-CI
  申请人：UNIV ILLINOIS

  公开号：WO2017120507A1

  公开（公告）日：2017-07-13

  Provided are compounds of formulae provided herein. The compounds may include pathway-preferential estrogens (PaPEs) derivatives with tissue-selective activities. Also provided are pharmaceutical compositions comprising the compounds, as well as methods of treating a disease or condition including administering the compounds. The disease or condition may include postmenopausal symptoms, cardiovascular disease, stroke, vascular disease, bone disease, metabolic disease, arthritis, osteoporosis, obesity, vasomotor/hot flush, cognitive decline, cancer including breast cancer.

  提供了本处所提供的化合物的化学式。这些化合物可能包括具有组织选择性活性的途径优先雌激素（PaPEs）衍生物。此外，还提供了包含这些化合物的药物组合物，以及治疗疾病或症状的方法，包括给予这些化合物。这种疾病或症状可能包括绝经后症状、心血管疾病、中风、血管疾病、骨疾病、代谢疾病、关节炎、骨质疏松症、肥胖、血管运动/潮热、认知能力下降、癌症包括乳腺癌。