5-bromo-2-chloromethylnaphthalene | 164065-74-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-bromo-2-chloromethylnaphthalene
• 英文别名: 1-Bromo-6-(chloromethyl)naphthalene
• CAS: 164065-74-1
• 化学式: C₁₁H₈BrCl
• 分子量: 255.542
• InChiKey: LFWMQDIMQWPURX-UHFFFAOYSA-N

物化性质

• 沸点：
  352.8±17.0 °C(Predicted)
• 密度：
  1.526±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  5-bromo-2-chloromethylnaphthalene 在 吡啶 、 氯化亚砜 、 盐酸羟胺 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 、 水 、 二甲基亚砜 、 乙腈 为溶剂， 反应 20.92h， 生成 4-[(5-bromo-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
• 作为产物：
  描述：

  5-溴-2-萘甲酸甲酯 在 氯化亚砜 、 二异丁基氢化铝 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 18.67h， 生成 5-bromo-2-chloromethylnaphthalene
  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

• Naphthalenylmethyl cycloalkenone acetic acids and analogs thereof useful
  申请人：American Home Products Corporation

  公开号：US05399588A1

  公开（公告）日：1995-03-21

  The compounds of this invention which have the formula: ##STR1## wherein: R.sup.1 and R.sup.2 are independently hydrogen, C.sub.1 -C.sub.8 alkyl, halogen, C.sub.1 -C.sub.8 alkoxy, or trifluoromethyl; R.sup.3 is --OH or --NHCO.sub.2 CH.sub.3 ; X is --CH.sub.2 -- or --OCH.sub.2 --; n is 1 or 2; or a pharmaceutically acceptable salt thereof, are useful in treating or inhibiting the long-term complications of diabetes such as diabetic retinopathy, nephropathy and neuropathy through the inhibition of the enzyme aldose reductase. Aldose reductase inhibitors have been shown to prevent the biochemical, functional and morphological changes induced by hyperglycemia.

  本发明的化合物具有以下公式：##STR1## 其中：R.sup.1 和 R.sup.2 独立地是氢、C.sub.1 -C.sub.8 烷基、卤素、C.sub.1 -C.sub.8 烷氧基或三氟甲基；R.sup.3 是--OH或--NHCO.sub.2 CH.sub.3；X 是--CH.sub.2--或--OCH.sub.2--；n 是1或2；或其药用盐，用于治疗或抑制糖尿病的长期并发症，如糖尿病视网膜病变、肾病和神经病变，通过抑制醛糖还原酶酶。已经证明醛糖还原酶抑制剂可以预防高血糖引起的生化、功能和形态学变化。
• Phenoxy acetic acids as aldose reductase inhibitors and
  申请人：American Home Products Corporation

  公开号：US05677342A1

  公开（公告）日：1997-10-14

  This invention relates to 4-formyl-2-(naphthalenylmethyl)phenoxyacetic acids and pharmaceutically acceptable salts thereof according to formula I below, pharmaceutical compositions thereof, a method of treating hyperglycemia due to non-insulin dependent diabetes mellitus, and a method of prevention or treatment of complications associated with diabetes. ##STR1## wherein the group A is selected from the group consisting of 1-naphthyl, 2-naphthyl, optionally substituted with alkyl of from one to six carbon atoms, fluorine, chlorine, bromine, iodine, trifluoromethyl, alkoxy of from one to six carbon atoms; R.sup.1 is hydrogen or alkyl of from one to six carbon atoms; R.sup.2 is selected from hydrogen, fluorine, chlorine, bromine, iodine, alkyl of from one to six carbon atoms, alkoxy of from one to six carbon atoms, and hydroxyl; or a pharmaceutically acceptable metal salt thereof.

  本发明涉及以下公式I所示的4-甲醛基-2-(萘基甲基)苯氧乙酸及其药学上可接受的盐、其制药组合物、治疗非胰岛素依赖型糖尿病所致高血糖的方法，以及预防或治疗与糖尿病相关的并发症的方法。其中，基团A选自1-萘基、2-萘基，可选地被烷基（烷基含1至6个碳原子）、氟、氯、溴、碘、三氟甲基、含1至6个碳原子的烷氧基取代；R1为氢或含1至6个碳原子的烷基；R2选自氢、氟、氯、溴、碘、含1至6个碳原子的烷基、含1至6个碳原子的烷氧基和羟基；或其药学上可接受的金属盐。
• Malamas, Michael S.; Hohman, Thomas C., Medicinal Chemistry Research, 1995, vol. 5, # 4, p. 245 - 254
  作者：Malamas, Michael S.、Hohman, Thomas C.

  DOI：——

  日期：——
• PHENOXY ACETIC ACIDS AS ALDOSE REDUCTASE INHIBITORS AND ANTIHYPERGLYCEMIC AGENTS
  申请人：AMERICAN HOME PRODUCTS CORPORATION

  公开号：EP0847379A1

  公开（公告）日：1998-06-17
• US5399588A
  申请人：——

  公开号：US5399588A

  公开（公告）日：1995-03-21