2-溴-1-(5-甲基-2-苯基-1,3-恶唑-4-基)乙酮 | 103788-62-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 2-溴-1-(5-甲基-2-苯基-1,3-恶唑-4-基)乙酮
• 英文名称: 4-bromoacetyl-5-methyl-2-phenyl-oxazole
• 英文别名: 2-bromo-1-(5-methyl-2-phenyloxazol-4-yl)ethanone；2-bromo-1-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethanone
• CAS: 103788-62-1
• 化学式: C₁₂H₁₀BrNO₂
• 分子量: 280.121
• InChiKey: RSBWHTQEZHZARK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  43.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-溴-1-(5-甲基-2-苯基-1,3-恶唑-4-基)乙酮 在 三乙基硅烷 、 sodium tetrahydroborate 、 sodium methylate 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 生成 (5-bromo-2-benzofuranyl)(5-methyl-2-phenyl-4-oxazolyl)methane
  参考文献：
  名称：

  Antihyperglycemic activity of new 1,2,4-oxadiazolidine-3,5-diones

  摘要：

  A series of 1,2,4-oxadiazolidine-3,5-diones was synthesized and evaluated as oral antihyperglycemic agents in the obese insulin resistant db/db and ob/ob mouse - the two models for Type 2 diabetes mellitus. The majority of the prepared methoxy- and ethoxy-linked oxazole 1,2,4-oxadiazolidine-3,5-diones normalized plasma glucose levels at the 100 mg kg(-1) oral dose in the db/db diabetic mouse model, and several amongst them reduced the glucose levels at the 20 mg kg(-1) oral dose. The most potent compounds in the db/db mouse model were also active in the ob/ob mouse model normalizing the plasma glucose levels at the 20 mg kg(-1) oral dose. The trifluoromethoxy analog 32 was the most active compound of the series, reducing significantly the plasma glucose levels at the 5 mg kg(-1) oral dose. Oxadiazole-tailed 1,2,4-oxadiazolidine-3,5-diones were also active in both the db/db and ob/ob diabetic mouse models normalizing plasma glucose levels at the 100 mg kg(-1) oral dose. (C) 2001 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(00)01191-0
• 作为产物：
  描述：

  2,3,4-戊三酮肟 (6ci,7ci,8ci,9ci) 在 盐酸 、 溴 、 溶剂黄146 、 锌 作用下， 以 氯仿 为溶剂， 生成 2-溴-1-(5-甲基-2-苯基-1,3-恶唑-4-基)乙酮
  参考文献：
  名称：

  Synthesis and spectral properties of 3-(2-aryl-5-methyl-1,3-oxazol- 4-yl)-2-(2,5-dimethylthiophen-3-yl)cyclopent-2-en-1-ones

  摘要：

  Alkylation of ethyl 4-(2,5-dimethylthiophen-3-yl)-3-oxobutanoate with 2-aryl-4-bromoacetyl-5-methyl-1,3-oxazole followed by decarboxylation cyclization of the intermediate, diketo ester affords the title photochromic compounds. Relationship between the fluorescent characteristics, thermal stability of photoinduced form as well as quantum yields of photochemical reactions and the structure of these compounds was evaluated.

  DOI：

  10.1016/j.mencom.2014.09.010

文献信息

• Indol-3-yl-carbonyl-spiro-piperidine derivatives as Vla receptor antagonists
  申请人：Bissantz Caterina

  公开号：US20070027173A1

  公开（公告）日：2007-02-01

  The invention relates to indol-3-yl-carbonyl-spiro-piperidine derivatives which act as V1a receptor antagonists and which are represented by Formula I: wherein the spiro-piperidine head group A and the residues R 1 , R 2 and R 3 are as defined herein. The invention further relates to pharmaceutical compositions containing such compounds, methods for preparing the compounds and pharmaceutical compositions, and their use in the treatment of dysmenorrhea, hypertension, chronic heart failure, inappropriate secretion of vasopressin, liver cirrhosis, nephrotic syndrome, obsessive compulsive disorder, anxious and depressive disorders.

  本发明涉及作为V1a受体拮抗剂的吲哚-3-基-甲酰基-螺环-哌啶衍生物，其由公式I表示：其中，螺环-哌啶头基A以及残基R1、R2和R3如本文所述定义。本发明进一步涉及含有此类化合物的药物组合物，制备化合物和药物组合物的方法，以及它们在治疗痛经、高血压、慢性心力衰竭、血管升压素不适当分泌、肝硬化、肾病综合征、强迫症、焦虑和抑郁障碍中的用途。
• Dialkylation of Ethyl 4-(Het)aryl-3-oxobutanoates as a Route to 5-(2-Oxoethyl)cyclopentenones
  作者：Andrey G. Lvov、Alexey V. Zakharov、Konstantin A. Lyssenko、Vadim V. Kachala、Valerii Z. Shirinian

  DOI：10.1055/s-0039-1689926

  日期：2019.7

  An unexplored ability of the long-known chemical transformation, Borsche’s cyclopentenone synthesis (the construction of a 1,4-diketone with subsequent base-induced cyclization), is reported. Double alkylation of ethyl 4-(het)aryl-3-oxobutanoates with 2-bromo-1-(het)arylethanones, with subsequent alkali treatment, provides access to cyclopentenones substituted with a 2-oxoethyl group at the 5-position

  报道了一种长期已知的化学转化的未知能力，即 Borsche 的环戊烯酮合成（构建 1,4-二酮和随后的碱诱导环化）。4-（杂）芳基-3-氧代丁酸乙酯与 2-溴-1-（杂）芳基乙酮的双烷基化，随后进行碱处理，提供在 5 位被 2-氧乙基取代的环戊烯酮。这些产物可能作为杂环化的有价值的合成子，并且通过合成 4H-环戊二烯 [b] 噻吩衍生物证明了这一特征。
• Thiazolidinedione derivatives
  申请人：BEECHAM GROUP PLC

  公开号：EP0299620A1

  公开（公告）日：1989-01-18

  A compound of formula (I): or a pharmaceutically acceptable salt thereof, wherein: A° represents nitrogen or a moiety wherein R1 represents hydrogen, alkyl or a substituted or unsubstituted aryl group; R2 represents a moiety R3-Y-Z- wherein R3 represents substituted or unsubstituted phenyl, substituted or unsubstituted pyridyl or a substituted or unsubstituted oxazolyl group, and Y represents -(CH2)n. wherein n represents zero or any integer in the range of 1 to 6 and Z represents -CH2-,-CH(OH)- or -CO-; Ra and Rb each represent hydrogen or Ra and Rb together represent a bond; A represents a residue of a benzene ring, the carbon atoms of the residue having in total up to four substituents; and X represents 0 or S; a process for preparing such a compound, a pharmaceutical composition containing such a compound and the use of the compound and composition in medicine.

  一种化合物的化学式（I）： 或其药学上可接受的盐，其中：A°代表氮或一个基团 其中 R1代表氢、烷基或一个取代或未取代的芳基； R2代表一个基团R3-Y-Z-，其中R3代表取代或未取代的苯基、取代或未取代的吡啶基或一个取代或未取代的噁唑基，Y代表-(CH2)n，其中n代表零或在1到6范围内的任意整数，Z代表-CH2-，-CH(OH)-或-CO-； Ra和Rb各自代表氢或Ra和Rb一起代表一个键； A代表苯环的残基，残基的碳原子总共最多有四个取代基； X代表0或S；一种制备这种化合物的方法，含有这种化合物的药物组合物以及在医学中使用该化合物和组合物。
• 3-aryl-2-hydroxypropionic acid derivatives and analogs as
  申请人：Pfizer Inc.

  公开号：US05232945A1

  公开（公告）日：1993-08-03

  A method of using certain 3-aryl-2-hydroxypropionic acid derivatives and analogs in the treatment of hypertension.

  使用某些3-芳基-2-羟基丙酸衍生物和类似物治疗高血压的方法。
• Hypoglycemic Activity of a Series of α-Alkylthio and α-Alkoxy Carboxylic Acids Related to Ciglitazone
  作者：Bernard Hulin、Linda S. Newton、Diana M. Lewis、Paul E. Genereux、E. Michael Gibbs、David A. Clark

  DOI：10.1021/jm960230h

  日期：1996.1.1

  The thiazolidinedione moiety of ciglitazone and its analogues can be replaced by an alpha-alkoxy or alpha-thioether carboxylic acid group. The influence of the nature of the R group, the length of the connector to the aromatic backbone of the molecule, and the stereochemistry have been studied. The most potent compounds have glucose-lowering activity at doses as low as 0.01 mg/kg.

  西格列酮的噻唑烷二酮部分及其类似物可以被α-烷氧基或α-硫醚羧酸基团取代。已经研究了R基团的性质，分子的芳族主链的连接体的长度以及立体化学的影响。最有效的化合物在低至0.01 mg / kg的剂量下具有降低葡萄糖的活性。