(5-溴-2-羟基苯基)-(1-苯基-1H-吡唑-4-基)酮 | 68287-72-9

• 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: (5-溴-2-羟基苯基)-(1-苯基-1H-吡唑-4-基)酮
• 中文别名: (5-溴-2-羟基苯)-(1-苯基-1H-吡唑-4-基)甲酮
• 英文名称: (5-bromo-2-hydroxyphenyl)-(1-phenyl-1H-pyrazol-4-yl)ketone
• 英文别名: (5-bromo-2-hydroxyphenyl)(1-phenyl-1H-pyrazol-4-yl)methanone；(5-Bromo-2-hydroxy-phenyl)-(1-phenyl-1H-pyrazol-4-yl)ketone；(5-bromo-2-hydroxyphenyl)-(1-phenylpyrazol-4-yl)methanone
• CAS: 68287-72-9
• 化学式: C₁₆H₁₁BrN₂O₂
• 分子量: 343.18
• InChiKey: MPZOVJOEZZCBKJ-UHFFFAOYSA-N

物化性质

• 熔点：
  143-148 °C(lit.)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  55.1
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• WGK Germany：
  3
• 危险标志：
  GHS07
• 危险性描述：
  H315,H319,H335
• 危险性防范说明：
  P261,P305 + P351 + P338

反应信息

• 作为反应物：
  描述：

  (5-溴-2-羟基苯基)-(1-苯基-1H-吡唑-4-基)酮 在 lithium hydroxide 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 、 丙酮 为溶剂， 反应 12.0h， 生成 2-[4-bromo-2-(1-phenylpyrazole-4-carbonyl)phenoxy]acetic Acid
  参考文献：
  名称：

  Novel Selective Orally Active CRTH2 Antagonists for Allergic Inflammation Developed from in Silico Derived Hits

  摘要：

  Hits from an in silico derived focused library for CRTH2 were transformed into highly selective antagonists with favorable ADME properties. Oral administration of 4-bromo-2-( 1-phenyl-1H-pyrazole-4-carbonyl) phenoxyacetic acid ( 19) inhibited peribronchial eosinophilia and mucus cell hyperplasia in a mouse model of allergic asthma, supporting the therapeutic potential of this novel compound class. In addition, this selective pharmacological tool compound provides further evidence for CRTH2 as a relevant therapeutic target for treatment of Th2- and eosinophil-related inflammation.

  DOI：

  10.1021/jm060657g
• 作为产物：
  描述：

  (E)-6-bromo-3-((2-phenylhydrazono)methyl)-4H-chromen-4-one 、 氢氧化钾 生成 (5-溴-2-羟基苯基)-(1-苯基-1H-吡唑-4-基)酮
  参考文献：
  名称：

  GHOSH C. K.; MUKHOPADHYAY K. K., J. INDIAN CHEM. SOC., 1978, 55, NO 1, 52-55

  摘要：

  DOI：

文献信息

• N-heterocycle carbene (NHC)-ligated cyclopalladated N,N-dimethylbenzylamine: a highly active, practical and versatile catalyst for the Heck–Mizoroki reaction
  作者：Guang-Rong Peh、Eric Assen B. Kantchev、Chi Zhang、Jackie Y. Ying

  DOI：10.1039/b821892g

  日期：——

  NHC-Pd catalyst, a triflate was coupled with diverse acrylate derivatives (nitrile, tert-butyl ester and amides) and styrene derivatives. The use of excess (>2 equiv.) of the aryl bromide and tert-butyl acrylate leads to mixture of tert-butyl β,β-diarylacrylate and tert-butyl cinnamate derivatives depending on the substitution pattern of the aryl bromide. Electron rich m- and p-substituted arylbromides

  催化剂的发展不仅促进了催化方案在学术和工业实验室中的广泛传播，该催化剂不仅具有高活性，而且还易于使用，对湿气，空气和长期储存稳定，易于大规模制备。在本文中，我们描述了由环钯N，N-二甲基苄胺（dmba）与N杂环卡宾1,3-双（甲磺酰基）咪唑-2-亚基（IMes）连接而介导的Heck-Mizoroki反应的方案标准。可以通过三组分，顺序，一锅法反应制得约100 g规模的预催化剂。N，N-二甲基苄胺，PdCl 2和IMes·HCl回流乙腈在空气中存在K 2 CO 3的情况下。这种单组分催化剂对空气，湿气和长期储存稳定，并且可以方便地作为储备溶液分配到NMP中。它介导0.1-2 mol％范围的试剂级NMP中的一系列芳基和杂芳基溴的Heck-Mizoroki反应，而无需严格的无水技术或手套箱，甚至在空气中也具有活性。该催化剂能够实现很高的催化活性（TON高达5.22×10 5），用于偶联失活的芳基溴化物，对溴苯甲醚，以t
• Facile synthesis of diazido-functionalized biaryl compounds as radioisotope-free photoaffinity probes by Suzuki–Miyaura coupling
  作者：Takamitsu Hosoya、Atsushi Inoue、Toshiyuki Hiramatsu、Hiroshi Aoyama、Takaaki Ikemoto、Masaaki Suzuki

  DOI：10.1016/j.bmc.2009.01.070

  日期：2009.3

  Suzuki–Miyaura coupling of 3-azido-5-(azidomethyl)phenylboronic acid pinacol ester with various aryl bromides affords corresponding diazido-functionalized biaryl compounds in good yields. This approach provides an easy access to radioisotope-free photoaffinity probes possessing biaryl structure. By using this method, we prepared a novel diazido-functionalized dantrolene analog, which showed selective

  将3-叠氮基-5-（叠氮基甲基）苯基硼酸频哪醇酯与各种芳基溴化物进行的Suzuki-Miyaura偶联，可以以良好的收率得到相应的二叠氮基官能化的联芳基化合物。这种方法可轻松访问具有联芳基结构的无放射性同位素的光亲和探针。通过使用这种方法，我们制备了一种新型的叠氮基官能化的双氢戊二烯类似物，其对小鼠骨骼肌肌浆网（SR）的生理性Ca 2+释放（PCR）具有选择性抑制作用，而不会影响Ca 2+诱导的Ca 2+释放（CICR）。
• 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。