4-(4-hydroxyphenyl)-4H-2,3-dihydrobenzothiopyran | 57480-10-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫铬烷
• 英文名称: 4-(4-hydroxyphenyl)-4H-2,3-dihydrobenzothiopyran
• 英文别名: 4p-Hydroxyphenyl-thiochromane；4-(3,4-dihydro-2H-thiochromen-4-yl)phenol
• CAS: 57480-10-1
• 化学式: C₁₅H₁₄OS
• 分子量: 242.342
• InChiKey: GYICTBUFOFEGTB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(4-hydroxyphenyl)-4H-2,3-dihydrobenzothiopyran 在 正丁基锂 、 N-环己基异丙基胺 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 生成 3-(3-Ethyl-phenyl)-2-methyl-2-(4-thiochroman-4-yl-phenoxy)-propionic acid ethyl ester
  参考文献：
  名称：

  Glucose Transport-Enhancing and Hypoglycemic Activity of 2-Methyl-2-phenoxy-3-phenylpropanoic Acids

  摘要：

  A series of 2-phenoxy-3-phenylpropanoic acids has been prepared which contains many potent hypoglycemic agents as demonstrated by assessing glucose lowering in ob/ob mice. Some compounds (32, 33, 59) normalize plasma glucose in this diabetic model at doses of approximately 1 mg/kg. The mechanism of action of these drugs may involve enhanced glucose transport, especially in fat cells, but the compounds do not stimulate GLUT4 translocation and do not increase the levels of GLUT1 or GLUT4 in vivo. Thus, these compounds may enhance the intrinsic activity of the glucose transporter GLUT1 or GLUT4. Some compounds also modestly decrease hepatocyte gluconeogenesis in vitro, but this is not likely to be a major contributor to the hypoglycemic effect observed in vivo. Likewise, a modest decrease in food consumption observed with some of these compounds was shown by a pair-feeding experiment not to be the primary cause of the hypoglycemia observed.

  DOI：

  10.1021/jm950364f
• 作为产物：
  描述：

  (4-溴苯氧基)叔丁基二甲基硅烷 在 Pd-BaSO₄ 盐酸 、 氢气 、 magnesium 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 25.0 ℃ 、317.16 kPa 条件下， 反应 72.0h， 生成 4-(4-hydroxyphenyl)-4H-2,3-dihydrobenzothiopyran
  参考文献：
  名称：

  Glucose Transport-Enhancing and Hypoglycemic Activity of 2-Methyl-2-phenoxy-3-phenylpropanoic Acids

  摘要：

  A series of 2-phenoxy-3-phenylpropanoic acids has been prepared which contains many potent hypoglycemic agents as demonstrated by assessing glucose lowering in ob/ob mice. Some compounds (32, 33, 59) normalize plasma glucose in this diabetic model at doses of approximately 1 mg/kg. The mechanism of action of these drugs may involve enhanced glucose transport, especially in fat cells, but the compounds do not stimulate GLUT4 translocation and do not increase the levels of GLUT1 or GLUT4 in vivo. Thus, these compounds may enhance the intrinsic activity of the glucose transporter GLUT1 or GLUT4. Some compounds also modestly decrease hepatocyte gluconeogenesis in vitro, but this is not likely to be a major contributor to the hypoglycemic effect observed in vivo. Likewise, a modest decrease in food consumption observed with some of these compounds was shown by a pair-feeding experiment not to be the primary cause of the hypoglycemia observed.

  DOI：

  10.1021/jm950364f

文献信息

• Phenoxyalkanol derivatives
  申请人：Merck Patent Gesellschaft mit beschrankter Haftung

  公开号：US04051173A1

  公开（公告）日：1977-09-27

  Phenoxylakanols of the formula ##STR1## wherein R.sup.1 is H or CH.sub.3 ; R.sup.2 is CH.sub.3 or C.sub.6 H.sub.5 ; R.sup.3 is 4-Hal-phenoxymethyl, 1,2,3,4-tetrahydro-1-naphthyl, 1-pyrryl, piperidino, isoindoline, 1,2,3,4-tetrahydroquinoline, 1,2,3,4-tetrahydro-1-R.sup.5 -4-quinolyl, 4-chromanyl, 4-thiochromanyl, or, when at least one of R.sup.1 and R.sup.2 is other than CH.sub.3, also Hal, phenyl, 4-Hal-phenyl or 4-Hal-phenoxy, wherein R.sup.4 is H or alkanoyl of 2-4 carbon atoms, R.sup.5 is H or CH.sub.3 and Hal if F, Cl or Br; and physiologically acceptable acid addition salts thereof possess pharmacological activity, particularly cholesterol, triglyceride and uric acid blood-level lowering activity and are also useful as intermediates for the production of the corresponding phenoxyacetic acids.

  公式为 ##STR1## 的Phenoxylakanols，其中 R.sup.1 为 H 或 CH.sub.3；R.sup.2 为 CH.sub.3 或 C.sub.6 H.sub.5；R.sup.3 为 4-Hal-phenoxymethyl、1,2,3,4-tetrahydro-1-naphthyl、1-pyrryl、piperidino、isoindoline、1,2,3,4-tetrahydroquinoline、1,2,3,4-tetrahydro-1-R.sup.5 -4-quinolyl、4-chromanyl、4-thiochromanyl，或者当至少有一个 R.sup.1 和 R.sup.2 不是 CH.sub.3 时，也可以是 Hal、phenyl、4-Hal-phenyl 或 4-Hal-phenoxy；其中 R.sup.4 为 H 或 2-4 碳原子的脂肪酰基，R.sup.5 为 H 或 CH.sub.3，如果 F、Cl 或 Br 则为 Hal；其生理上可接受的酸盐具有药理活性，特别是降低胆固醇、三酰甘油和尿酸血液水平的活性，并且还可用作制备相应的苯氧乙酸的中间体。
• US3992386A
  申请人：——

  公开号：US3992386A

  公开（公告）日：1976-11-16
• US4051173A
  申请人：——

  公开号：US4051173A

  公开（公告）日：1977-09-27
• US4051170A
  申请人：——

  公开号：US4051170A

  公开（公告）日：1977-09-27
• US4053626A
  申请人：——

  公开号：US4053626A

  公开（公告）日：1977-10-11