2,3-dichloro-4-<(4-nitrophenyl)sulfenyl>phenol | 87181-27-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2,3-dichloro-4-<(4-nitrophenyl)sulfenyl>phenol
• 英文别名: 2,3-Dichloro-4-(p-nitrophenylsulfenyl)phenol；2,3-dichloro-4-(4-nitrophenyl)sulfanylphenol
• CAS: 87181-27-9
• 化学式: C₁₂H₇Cl₂NO₃S
• 分子量: 316.164
• InChiKey: HBMBRTRUUOLRLR-UHFFFAOYSA-N

物化性质

• 熔点：
  202-204 °C
• 沸点：
  474.8±45.0 °C(Predicted)
• 密度：
  1.61±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  91.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,3-dichloro-4-<(4-nitrophenyl)sulfenyl>phenol 在 sulfided Pt/C 吡啶 、 盐酸 、 硫酸 、 2,3-二氯碘苯 、 水 、 氢气 、 potassium carbonate 、 sodium sulfate 、 三乙胺 、 N,N-二异丙基乙胺 、 sodium nitrite 作用下， 以 乙醇 、 二氯甲烷 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 丁酮 为溶剂， 反应 14.0h， 生成 methyl <2,3-dichloro-4-<<3-(aminomethyl)-4-hydroxyphenyl>sulfinyl>phenoxy>acetate hydrochloride
  参考文献：
  名称：

  [(Aminomethyl)aryloxy]acetic acid esters. A new class of high-ceiling diuretics. 3. Variation in the bridge between the aromatic rings to complete mapping of the receptor

  摘要：

  Continued structural evaluation of the [(aminomethyl)aryloxy]acetic ester diuretics has produced a series of compounds in which the functional group that bridges the two aromatic rings has been varied. Diuretic screening of these analogues in rats indicates that the keto group can be effectively replaced with an ether or thio ether function with a slight increase in potency, whereas the methylene and sulfoxide linking groups lead to diminished saluretic potency. Replacement with either -SO2-, -COCO-, -CH2O-, -CONH- or direct bond results in a loss of activity. Although the series was designed according to QSAR criteria, the traditional linear free-energy properties of these compounds do not correlate with diuretic potency. However, conformational analysis of the series by potential energy calculations indicates that all active compounds have an accessible conformation that matches the bridge atom-carboxylate distance of the very potent dihydrobenzofuran analogue 56. Conformational calculations of several compounds in which the aminomethyl group was varied suggests that the active conformation is probably a low-energy conformation. Consideration of rotation about the bridge could not distinguish between two possible orientations of the aminomethyl ring in the active conformation. However, there is a quantitative negative linear correlation between diuretic potency and the protrusion into space of the group that bridges the two aromatic rings.

  DOI：

  10.1021/jm00379a016
• 作为产物：
  描述：

  2,3-dichloro-4-ethoxybenzenesulfonyl chloride 在 lithium aluminium tetrahydride 、 三氯化铝 、 potassium carbonate 作用下， 以 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 2,3-dichloro-4-<(4-nitrophenyl)sulfenyl>phenol
  参考文献：
  名称：

  [(Aminomethyl)aryloxy]acetic acid esters. A new class of high-ceiling diuretics. 3. Variation in the bridge between the aromatic rings to complete mapping of the receptor

  摘要：

  Continued structural evaluation of the [(aminomethyl)aryloxy]acetic ester diuretics has produced a series of compounds in which the functional group that bridges the two aromatic rings has been varied. Diuretic screening of these analogues in rats indicates that the keto group can be effectively replaced with an ether or thio ether function with a slight increase in potency, whereas the methylene and sulfoxide linking groups lead to diminished saluretic potency. Replacement with either -SO2-, -COCO-, -CH2O-, -CONH- or direct bond results in a loss of activity. Although the series was designed according to QSAR criteria, the traditional linear free-energy properties of these compounds do not correlate with diuretic potency. However, conformational analysis of the series by potential energy calculations indicates that all active compounds have an accessible conformation that matches the bridge atom-carboxylate distance of the very potent dihydrobenzofuran analogue 56. Conformational calculations of several compounds in which the aminomethyl group was varied suggests that the active conformation is probably a low-energy conformation. Consideration of rotation about the bridge could not distinguish between two possible orientations of the aminomethyl ring in the active conformation. However, there is a quantitative negative linear correlation between diuretic potency and the protrusion into space of the group that bridges the two aromatic rings.

  DOI：

  10.1021/jm00379a016

文献信息

• Diphenyl ether, diphenyl thioether and diphenyl methane phenol mannich
  申请人：Abbott Laboratories

  公开号：US04389416A1

  公开（公告）日：1983-06-21

  Described are compounds of the formula ##STR1## wherein R is hydrogen, loweralkyl, aminomethyl or halo; R.sub.1 is carboxy, carboxyloweralkyl, aminocarbonyl, hydroxymethyl, anilinomethyl, or aminomethyl; A is oxygen, CH.sub.2, Sulfur or a single bond; X is oxygen, CH.sub.2, sulfur or sulfoxide; and Y is hydrogen, loweralkyl or halo and may be the same or different, and pharmaceutically acceptable salts thereof. The compounds are effective as diuretic agents.

  本发明涉及的是化合物，其化学式为##STR1##其中R为氢，低碳基，氨甲基或卤素; R.sub.1为羧基，羧基低碳基，氨基甲酰，羟甲基，苯胺甲基或氨基甲基; A为氧，CH.sub.2，硫或单键; X为氧，CH.sub.2，硫或亚砜; Y为氢，低碳基或卤素，可以相同也可以不同，以及其药学上可接受的盐。这些化合物作为利尿剂具有良好的效果。
• PLATTNER, J. J.;MARTIN, Y. C.;SMITAL, J. R.;LEE, C. -M.;FUNG, A. K. L.;HO+, J. MED. CHEM., 1985, 28, N 1, 79-93
  作者：PLATTNER, J. J.、MARTIN, Y. C.、SMITAL, J. R.、LEE, C. -M.、FUNG, A. K. L.、HO+

  DOI：——

  日期：——
• US4389416A
  申请人：——

  公开号：US4389416A

  公开（公告）日：1983-06-21
• [(Aminomethyl)aryloxy]acetic acid esters. A new class of high-ceiling diuretics. 3. Variation in the bridge between the aromatic rings to complete mapping of the receptor
  作者：Jacob J. Plattner、Yvonne C. Martin、Jill R. Smital、Cheuk Man Lee、Anthony K. L. Fung、Bruce W. Horrom、Steven R. Crowley、Andre G. Pernet、Paul R. Bunnell、Ki H. Kim

  DOI：10.1021/jm00379a016

  日期：1985.1

  Continued structural evaluation of the [(aminomethyl)aryloxy]acetic ester diuretics has produced a series of compounds in which the functional group that bridges the two aromatic rings has been varied. Diuretic screening of these analogues in rats indicates that the keto group can be effectively replaced with an ether or thio ether function with a slight increase in potency, whereas the methylene and sulfoxide linking groups lead to diminished saluretic potency. Replacement with either -SO2-, -COCO-, -CH2O-, -CONH- or direct bond results in a loss of activity. Although the series was designed according to QSAR criteria, the traditional linear free-energy properties of these compounds do not correlate with diuretic potency. However, conformational analysis of the series by potential energy calculations indicates that all active compounds have an accessible conformation that matches the bridge atom-carboxylate distance of the very potent dihydrobenzofuran analogue 56. Conformational calculations of several compounds in which the aminomethyl group was varied suggests that the active conformation is probably a low-energy conformation. Consideration of rotation about the bridge could not distinguish between two possible orientations of the aminomethyl ring in the active conformation. However, there is a quantitative negative linear correlation between diuretic potency and the protrusion into space of the group that bridges the two aromatic rings.