4-[(3-methyl-2-naphthalenyl)methyl]-3H-1,2,3,5-oxathiadiazole 2-oxide

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-[(3-methyl-2-naphthalenyl)methyl]-3H-1,2,3,5-oxathiadiazole 2-oxide
• 英文别名: 4-[(3-methylnaphthalen-2-yl)methyl]-5H-1,2,3,5-oxathiadiazole 2-oxide
• 化学式: C₁₃H₁₂N₂O₂S
• 分子量: 260.316
• InChiKey: KGVJYCNHKKGCRR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  87.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-hydroxymethyl-3-methylnaphthalene 在 吡啶 、 氯化亚砜 、 盐酸羟胺 、 sodium methylate 、 zinc(II) chloride 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 、 二甲基亚砜 、 乙腈 为溶剂， 反应 21.59h， 生成 4-[(3-methyl-2-naphthalenyl)methyl]-3H-1,2,3,5-oxathiadiazole 2-oxide
  参考文献：
  名称：

  Antihyperglycemic activity of novel naphthalenylmethyl-3H-1,2,3,5-oxathiadiazole 2-oxides

  摘要：

  A series of naphthalenyl 3H-1,2,3,5-oxathiadiazole 2-oxides was prepared and tested for antihyperglycemic activity in the db/db mouse, a model for type 2 (non-insulin dependent) diabetes mellitus. Substitution at the 1-, 5-, or 8-positions of the naphthalene ring with a halogen was found to be beneficial to antihyperglycemic activity. 4-[(5-Chloronaphthalen-2-yl)methyl]-3H-1,2,3,5-oxathiadiazole 2-oxide (45), one of the most potent compounds in this series, was selected for further pharmacological evaluation.

  DOI：

  10.1021/jm00069a006

文献信息

• Naphthalene derivatives
  申请人：AMERICAN HOME PRODUCTS CORPORATION

  公开号：EP0393941A1

  公开（公告）日：1990-10-24

  This invention relates to novel [(substituted naphthalenyl)alkyl]-3H-1,2,3,5-oxathiadiazole 2-oxides of formula wherein n is 0 to 4 and R¹ and R² have specified meanings, and their salts. The compounds have pharmaceutical properties which render them beneficial for the treatment of diabetes mellitus and associated conditions.

  本发明涉及新型[(取代的萘基)烷基]-3H-1,2,3,5-噁二唑 2-氧化物，其式为 其中 n 为 0 至 4，R¹ 和 R² 具有特定含义，以及它们的盐类。这些化合物具有药物特性，有利于治疗糖尿病及相关疾病。
• US4897405A
  申请人：——

  公开号：US4897405A

  公开（公告）日：1990-01-30
• Antihyperglycemic activity of novel naphthalenylmethyl-3H-1,2,3,5-oxathiadiazole 2-oxides
  作者：John W. Ellingboe、Louis J. Lombardo、Thomas R. Alessi、Thomas T. Nguyen、Frieda Guzzo、Charles J. Guinosso、James Bullington、Eric N. C. Browne、Jehan F. Bagli

  DOI：10.1021/jm00069a006

  日期：1993.8

  A series of naphthalenyl 3H-1,2,3,5-oxathiadiazole 2-oxides was prepared and tested for antihyperglycemic activity in the db/db mouse, a model for type 2 (non-insulin dependent) diabetes mellitus. Substitution at the 1-, 5-, or 8-positions of the naphthalene ring with a halogen was found to be beneficial to antihyperglycemic activity. 4-[(5-Chloronaphthalen-2-yl)methyl]-3H-1,2,3,5-oxathiadiazole 2-oxide (45), one of the most potent compounds in this series, was selected for further pharmacological evaluation.