5-溴-N-苯基-2-糠酰胺 | 58217-60-0

• 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-N-苯基-2-糠酰胺
• 英文名称: 5-bromo-furan-2-carboxylic acid anilide
• 英文别名: 5-Brom-furan-2-carbonsaeure-anilid；N-phenyl-5-bromofuran-2-carboxamide；5-bromo-N-phenylfuran-2-carboxamide
• CAS: 58217-60-0
• 化学式: C₁₁H₈BrNO₂
• mdl: MFCD00454504
• 分子量: 266.094
• InChiKey: WYJOTRPYPMADNJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  42.2
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2932190090

反应信息

• 作为反应物：
  描述：

  5-溴-N-苯基-2-糠酰胺 以55%的产率得到
  参考文献：
  名称：

  RAI, USHA KUMARI;SHANKER, BIRJA;SINGH, SUJAN;RAO, R. BALAJI, INDIAN J. CHEM. B, 27,(1988) N 7, C. 674-675

  摘要：

  DOI：
• 作为产物：
  描述：

  5-溴-2-糠酸 在 氯化亚砜 、 三乙胺 作用下， 以 苯 为溶剂， 反应 9.0h， 生成 5-溴-N-苯基-2-糠酰胺
  参考文献：
  名称：

  Antimuscarinic 3-(2-Furanyl)quinuclidin-2-ene Derivatives:  Synthesis and Structure−Activity Relationships

  摘要：

  A series of 25 derivatives of the muscarinic antagonist 3-(2-furanyl)quinuclidin-2-ene (4) was synthesized and evaluated for muscarinic and antimuscarinic properties. Substitution at all three positions of the furan ring has been investigated. The affinities of the new compounds were determined by competition experiments in homogenates of cerebral cortex, heart, parotid gland, and urinary bladder from guinea pigs using (-)-[H-3]-3-quinuclidinyl benzilate as the radioligand, and the antimuscarinic potency was determined in a functional assay on isolated guinea pig urinary bladder using carbachol as the agonist. Several of the novel derivatives displayed high muscarinic affinities. Whereas the affinity of lead compound 4 for cortical muscarinic receptors is moderate (K-i 300 nM), it is much higher for the 6-methyl (49; K-i = 12 nM), 5-ethyl (52; K-i = 7.4 nM), 5-bromo (33; K-i = 6.4 nM), and 3-phenyl (49; K-i = 2.8 nM) substituted derivatives. The substituent-induced increases in affinity do not appear to be additive as a 5-bromo-3-phenyl (54), and a 5-methyl-3-phenyl (55) substitution pattern only slightly increases affinity (K-i = 1.55 and 2.39 nM, respectively). The conformational preferences of the 3-phenyl (49) and 5-phenyl (51) derivatives were studied by X-ray crystallography and molecular mechanics calculations. Because of the observed high affinity of 49, a series of 16 meta-and para-substituted analogues of 49 was synthesized and tested. derivative (68) exhibited more than 10-fold improvement in affinity as compared to 49. The structure-activity relationships of the new series are well described with QSAR and CoMFA models.

  DOI：

  10.1021/jm970346t

文献信息

• High-Load, Soluble Oligomeric Carbodiimide:  Synthesis and Application in Coupling Reactions
  作者：Mianji Zhang、Punitha Vedantham、Daniel L. Flynn、Paul R. Hanson

  DOI：10.1021/jo048870c

  日期：2004.11.1

  A facile preparation of a high-load, soluble oligomeric alkyl cyclohexylcarbodiimide (OACC) reagent via ROM polymerization from commercially available starting materials is described. This reagent is exploited as a coupling reagent for esterification, amidation, and dehydration of carboxylic acids (aliphatic and aromatic) with an assortment of alcohols (aliphatic primary, secondary, and benzylic),

  描述了通过ROM聚合由市售的起始原料容易地制备高负荷的可溶性低聚烷基环己基碳二亚胺（OACC）试剂的方法。该试剂被用作偶联试剂，用于将羧酸（脂族和芳族）与各种醇（脂族伯，仲和苄基），硫醇，酚和胺（脂族伯，仲，分别是苄基和芳族/苯胺）。偶合事件发生后，用适当的溶剂（Et 2 O，MeOH或EtOAc）沉淀，然后通过SPE过滤，可提供具有极佳收率和纯度的产物。
• NOVEL HETEROCYCLIC DERIVATIVES AS M-GLU5 ANTAGONISTS
  申请人：Leonardi Amedeo

  公开号：US20090042841A1

  公开（公告）日：2009-02-12

  This invention relates to novel heterocyclic compounds having selective affinity for the mGlu5 subtype of metabotropic receptors, pharmaceutical compositions thereof and uses for such compounds and compositions in the treatment of lower urinary tract disorders, such as neuromuscular dysfunction of the lower urinary tract, and in the treatment of migraine and gastroesophagael reflux disease (GERD).

  本发明涉及一种新型杂环化合物，其具有选择性亲和力，适用于代谢型受体mGlu5亚型，以及该类化合物的制药组合物及其在治疗下尿路障碍（例如下尿路神经肌肉功能障碍）、偏头痛和胃食管反流病（GERD）方面的用途。
• Heterocyclic derivatives as M-GLU5 antagonists
  申请人：Leonardi Amedeo

  公开号：US08518916B2

  公开（公告）日：2013-08-27

  This invention relates to novel heterocyclic compounds having selective affinity for the mGlu5 subtype of metabotropic receptors, pharmaceutical compositions thereof and uses for such compounds and compositions in the treatment of lower urinary tract disorders, such as neuromuscular dysfunction of the lower urinary tract, and in the treatment of migraine and gastroesophagael reflux disease (GERD).

  本发明涉及新型杂环化合物，具有对代谢型受体mGlu5亚型的选择性亲和力，其制药组合物以及在治疗下尿路障碍，如下尿路神经肌肉功能障碍，以及治疗偏头痛和胃食管反流病（GERD）中使用这些化合物和组合物的用途。
• REDUCTION OF THE 2-NITROPHENYL ESTERS OF CERTAIN ACIDS
  作者：L. CHAS. RAIFORD、WILLIAM G. HUEY

  DOI：10.1021/jo01206a011

  日期：1941.11
• Rai, Usha Kumari; Mishra, S K; Shanker, Brija, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 6, p. 618 - 623
  作者：Rai, Usha Kumari、Mishra, S K、Shanker, Brija、Singh, Sujan、Rao, R Balaji

  DOI：——

  日期：——