5-bromo-α-(5-methyl-2-phenyloxazol-4-yl)-2-benzofuranmethanol | 132672-20-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-bromo-α-(5-methyl-2-phenyloxazol-4-yl)-2-benzofuranmethanol
• 英文别名: (5-bromo-2-benzofuranyl)(5-methyl-2-phenyl-4-oxazolyl)methanol；2-[1-(2-Phenyl-5-methyloxazol-4-yl)-1-hydroxymethyl]-5-bromobenzofuran；2-(2-Phenyl-5-methyloxazol-4-ylhydroxymethyl) 5-bromobenzofuran；2-(2-Phenyl-5-methyloxazol-4-ylhydroxymethyl)-5-bromobenzofuran；(5-Bromo-1-benzofuran-2-yl)-(5-methyl-2-phenyl-1,3-oxazol-4-yl)methanol
• CAS: 132672-20-9
• 化学式: C₁₉H₁₄BrNO₃
• 分子量: 384.229
• InChiKey: SYOYAMCBTABURM-UHFFFAOYSA-N

物化性质

• 熔点：
  152-154 °C
• 沸点：
  545.0±60.0 °C(Predicted)
• 密度：
  1.490±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  59.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-bromo-α-(5-methyl-2-phenyloxazol-4-yl)-2-benzofuranmethanol 在 三乙基硅烷 、 三氟乙酸 作用下， 以 乙酸乙酯 为溶剂， 生成 (5-bromo-2-benzofuranyl)(5-methyl-2-phenyl-4-oxazolyl)methane
  参考文献：
  名称：

  Oxazolidinedione hypoglycemic agents

  摘要：

  式##STR1##中R为环烷基或芳基；R.sub.1为烷基，X为O或C.dbd.O；A为O或S；B为N或CH的化合物可用作降糖药。

  公开号：

  US05498621A1
• 作为产物：
  描述：

  2-溴-1-(5-甲基-2-苯基-1,3-恶唑-4-基)乙酮 在 sodium tetrahydroborate 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 为溶剂， 反应 1.0h， 生成 5-bromo-α-(5-methyl-2-phenyloxazol-4-yl)-2-benzofuranmethanol
  参考文献：
  名称：

  Benzyloxazolidine-2,4-diones as potent hypoglycemic agents

  摘要：

  A series of benzyloxazolidine-2,4-diones, containing oxazole-based side chains, were found to lower blood glucose levels in the genetically obese ob/ob mouse. Incorporation of a benzofuran structural element in these compounds provides greatly enhanced in vivo potency. The syntheses and structure-activity relationships for this series are detailed.

  DOI：

  10.1021/jm00109a003

文献信息

• 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。
• Antihyperglycemic activity of new 1,2,4-oxadiazolidine-3,5-diones
  作者：M Malamas

  DOI：10.1016/s0223-5234(00)01191-0

  日期：2001.1

  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.
• DOW, ROBERT L.;BECHLE, BRUCE M.;CHOU, THOMAS T.;CLARK, DAVID A.;HULIN, BE+, J. MED. CHEM., 34,(1991) N, C. 1538-1544
  作者：DOW, ROBERT L.、BECHLE, BRUCE M.、CHOU, THOMAS T.、CLARK, DAVID A.、HULIN, BE+

  DOI：——

  日期：——
• HYPOGLYCEMIC HYDROXYUREA DERIVATIVES
  申请人：PFIZER INC.

  公开号：EP0544696B1

  公开（公告）日：1995-01-11
• THIAZOLIDINEDIONE HYPOGLYCEMIC AGENTS
  申请人：PFIZER INC.

  公开号：EP0591252A1

  公开（公告）日：1994-04-13