(2-羟基-5-甲基苯基)(1-苯基-1H-吡唑-4-基)甲酮 | 68430-93-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (2-羟基-5-甲基苯基)(1-苯基-1H-吡唑-4-基)甲酮
• 英文名称: (2-hydroxy-5-methylphenyl)-(1-phenyl-1H-pyrazol-4-yl)methanone
• 英文别名: (2-hydroxy-5-methyl-phenyl)-(1-phenyl-1H-pyrazol-4-yl)-methanone；(2-hydroxy-5-methylphenyl)(1-phenyl-1H-pyrazol-4-yl)methanone；(2-hydroxy-5-methylphenyl)-(1-phenylpyrazol-4-yl)methanone
• CAS: 68430-93-3
• 化学式: C₁₇H₁₄N₂O₂
• 分子量: 278.31
• InChiKey: VYXJMOPDZFQVSZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  55.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2-羟基-5-甲基苯基)(1-苯基-1H-吡唑-4-基)甲酮 在 sodium ethanolate 、 potassium carbonate 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 13.0h， 生成 5-Methyl-3-(1-phenyl-1H-pyrazol-4-yl)-benzofuran-2-carboxylic acid
  参考文献：
  名称：

  Reddy, G. Jagath; Sbitha, G.; Rao, A. V. Subba, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1984, vol. 23, # 1, p. 99 - 100

  摘要：

  DOI：
• 作为产物：
  描述：

  6-甲基-4-氧-4H-1-苯并吡喃-3-甲醛 在 对甲苯磺酸 作用下， 以 吡啶 、 苯 为溶剂， 反应 13.0h， 生成 (2-羟基-5-甲基苯基)(1-苯基-1H-吡唑-4-基)甲酮
  参考文献：
  名称：

  Ghosh, Chandra Kanta; Bandyopadhyay, Chandrakanta; Morin, Christophe, Journal of the Chemical Society. Perkin transactions I, 1983, p. 1989 - 1994

  摘要：

  DOI：

文献信息

• <i>In vitro</i> cytotoxicity of hydrazones, pyrazoles, pyrazolo-pyrimidines, and pyrazolo-pyridine synthesized from 6-substituted 3-formylchromones
  作者：Elier Galarraga、Neudo Urdaneta、Keily J. Gutierrez、Julio C. Herrera

  DOI：10.1515/znb-2014-0236

  日期：2015.5.1

  Pyrazoles 4a–f, hydrazones 5a–c and 6a–c, pyrazolo[1,5-a]pyrimidines 7a, b, and pyrazolo[3,4-b]pyridine 8 were prepared in good yields (80–95 %) from the reaction of 6-substituted (H, Me, F) 3-formylchromones 1a–c with N-substituted hydrazines 2a–c and aminopyrazole 3. The cytotoxicity of the synthesized compounds was assessed through the brine shrimp lethality assay. IC₅₀ values were between 80 and 300 μm. Fluorine substitution decreased IC₅₀ values.

  通过6-取代（H，Me，F）3-甲酰基香豆素 1a–c 与 N-取代的肼 2a–c 和氨基吡唑 3 反应，制备了吡唑 4a–f，肼酮 5a–c 和 6a–c，吡唑并[1,5-a]嘧啶 7a，b，和吡唑并[3,4-b]吡啶 8，产率良好（80–95%）。通过盐水虾致死实验评估了合成化合物的细胞毒性。IC₅₀ 值在80和300 μm 之间。氟取代降低了IC₅₀ 值。

• SYNTHESIS OF SOME NEW 3-BENZOPYRANOPYRIDINYL AND 3-PYRAZOLYL 1,2-BENZISOXAZOLES FROM o-HYDROXYHETEROARYL KETONES DERIVED FROM 3- FORMYLCHROMONE
  作者：G. Jagath Reddy、D. Latha、C. Thirupathaiah、K. Srinivasa Rao

  DOI：10.1515/hc.2003.9.4.391

  日期：2003.1

  (2a-r). Reaction of 1 with Phenylhydrazine gives Vol. 9, No. 4, 2003 Synthesis of some new 3-benzo pyraopyridinyl and 3-pyrazolyl 1,2-benzisoxazoles from o-hydroxy heteroarylketones derivedfrom 3-formylchromone hydroxybenzoylpyrazoles (6a-e) in good yields. The corresponding o-hydroxyketoximes 3a-q and 7a-e were obtained from o-hydroxyketones 2a-r and 6a-e by refluxing with hydroxylamine hydrochloride in

  一系列 3-苯并吡喃并吡啶基和吡唑基 1,2-苯并异恶唑 (5 & 9) 已从 3-甲酰基色酮 (1) 衍生的邻羟基芳基酮 (2 & 6) 制备。介绍 各种 3-取代 1,2-苯并异恶唑已被报道具有生理特性，例如抗惊厥和解痉活性。最近有报道称，两种 3-哌啶基取代的苯并异恶唑，即阿巴哌酮盐酸盐和伊潘立酮显示出有希望的抗精神病活性。此外，据报道几种吡唑衍生物和苯并吡喃并吡啶具有多种类型的生物活性。此外，由于存在不饱和酮基，3-甲酰基色酮 1 是一种非常活泼的中间体，在 C3 上有一个共轭的第二个羰基，在 C2 上有一个非常活泼的中心，这允许迈克尔加成亲核试剂并打开 γ-吡喃酮环。这些特性使 1 成为一种多功能合成子，可以很容易地从中获得各种邻羟基杂芳基酮。继续我们对基于 3-甲酰基色酮 (1) 的杂环的研究，并考虑到与 1,2-苯并异恶唑、吡唑和苯并吡喃吡啶相关的生物学特性，我们对从中间体邻羟基杂芳基酮合成
• CRTH2 Receptor Ligands For Medicinal Uses
  申请人：Ulven Trond

  公开号：US20090099189A1

  公开（公告）日：2009-04-16

  Compounds of formula (I) are useful for the treatment of disease responsive to modulation of CRTH2 receptor activity, such as asthma, rhinitis, allergic airway syndrome, and allergic rhinobronchitis, wherein A represents a carboxyl group —COON, or a carboxyl bioisostere; A 1 , is hydrogen or methyl; ring Ar 1 is an optionally substituted phenyl ring 5- or 6-membered monocyclic heteroaryl ring, in which AA 1 CHO— and L2 are linked to adjacent ring atoms; rings Are 2 , Ar 3 each independently represent a phenyl or 5- or 6-membered monocyclic heteroaryl ring, or a bicyclic ring system consisting of a 5- or 6-membered carbocyclic or heterocyclic ring which is benz-fused or fused to a 5- or 6-membered monocyclic heteroaryl ring, said ring or ring system being optionally substituted; t is 0 or 1; L2 and L3 are linker radicals as defined in the description.

  式(I)的化合物可用于治疗对CRTH2受体活性调节敏感的疾病，例如哮喘、鼻炎、过敏性气道综合症和过敏性鼻支气管炎，其中A代表羧基—COON或羧基生物同位素；A1为氢或甲基；环Ar1是一个可选取代的苯环5-或6-成员的单环杂环，其中AA1CHO—和L2与相邻的环原子连接；环Are2，Ar3各自独立地表示一个苯环或5-或6-成员的单环杂环，或由一个5-或6-成员的碳环或杂环组成的双环系统，该环或环系统被苯并或与一个5-或6-成员的单环杂环融合，该环或环系统是可选取代的；t为0或1；L2和L3是如描述中所定义的连接基团。
• CRTH2 receptor ligands for medicinal uses
  申请人：Ulven Trond

  公开号：US20110269763A1

  公开（公告）日：2011-11-03

  Compounds of formula (I) are useful for the treatment of disease responsive to modulation of CRTH2 receptor activity, such as asthma, rhinitis, allergic airway syndrome, and allergic rhinobronchitis: wherein A represents a carboxyl group —COOH, or a carboxyl bioisostere; A 1 is hydrogen or methyl; ring Ar 1 is an optionally substituted phenyl ring or 5- or 6-membered monocyclic heteroaryl ring, in which AA 1 CHO— and L2 are linked to adjacent ring atoms; rings Ar 2 , Ar 3 each independently represent a phenyl or 5- or 6-membered monocyclic heteroaryl ring, or a bicyclic ring system consisting of a 5- or 6-membered carbocyclic or heterocyclic ring which is benz-fused or fused to a 5- or 6-membered monocyclic heteroaryl ring, said ring or ring system being optionally substituted; t is 0 or 1; L2 and L3 are linker radicals as defined in the description.

  式(I)的化合物可用于治疗对CRTH2受体活性调节敏感的疾病，例如哮喘、鼻炎、过敏性气道综合症和过敏性鼻支气管炎：其中A代表羧基—COOH或羧基生物同位素；A1为氢或甲基；环Ar1为可选取代的苯环或5-或6-成员的单环杂环，其中AA1CHO—和L2连接到相邻的环原子上；环Ar2、Ar3各自独立地表示苯环或5-或6-成员的单环杂环，或由5-或6-成员的碳环或杂环组成的双环系统，该环或环系统是苯并或与5-或6-成员的单环杂环融合，该环或环系统是可选的取代；t为0或1；L2和L3是如描述中定义的连接基。
• CRTH2 Receptor Ligands for Medical Use
  申请人：7TM Pharma A/S

  公开号：EP2336113A1

  公开（公告）日：2011-06-22

  4-Bromo-2-[1-(2,6-dichlorophenyl)-1H-pyrazole-4-carbonyl]phenoxyl acetic acid is useful for the treatment of disease responsive to modulation of CRTH2 receptor activity, such as asthma, rhinitis, allergic airway syndrome, and allergic rhinobronchitis.

  4-溴-2-[1-（2,6-二氯苯基）-1H-吡唑-4-甲酰基]苯氧乙酸可用于治疗对调节 CRTH2 受体活性有反应的疾病，如哮喘、鼻炎、过敏性气道综合征和过敏性鼻支气管炎。