4-sulfamoyl-N-(3-morpholinopropyl)benzamide | 1073637-75-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-sulfamoyl-N-(3-morpholinopropyl)benzamide
• 英文别名: 4-sulfamoyl-N-(morpholinopropyl)benzamide；4-Sulfamoyl-N-(3-morpholinopropyl)benzamide (I-1)；N-(3-morpholin-4-ylpropyl)-4-sulfamoylbenzamide
• CAS: 1073637-75-8
• 化学式: C₁₄H₂₁N₃O₄S
• 分子量: 327.404
• InChiKey: LAOOSMTXTNZTDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  110
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-sulfamoyl-N-(3-morpholinopropyl)benzamide 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 以59%的产率得到4-sulfamoyl-N-(3-morpholinopropyl)-benzamide hydrochloride
  参考文献：
  名称：

  Synthesis, crystal and molecular structure of two biologically active aromatic sulfonamides and their hydrochloride salts

  摘要：

  4-Sulfamoyl-N-(3-morpholinopropyl) benzamide (P10), N-(3-morpholinopropyl)benzene-1,4-disulfonamide (P20) and their hydrochloride salts (P11 and P22) were prepared. The X-ray molecular structure of these compounds was determined. The gas-phase structure of these drugs was computed using Becke3LYP/6-31G(d) and Becke3LYP/6-311 + G(d,p) model chemistries. The conformational behavior of these systems in water was examined using the solvation CPCM model. In the solid state, gas phase and in solution the conformations of the basic compounds P10 and P20 possess a characteristic L-shaped structure stabilized via an intramolecular hydrogen bonding system of the N-H center dot center dot center dot N type. This hydrogen bond is not present in P11 and P22. A network of intermolecular hydrogen bonds mediated by the Cl atoms and crystal-packing forces in P11 and P22 stabilize a more extended structure in the solid state. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2010.03.013
• 作为产物：
  描述：

  对羧基苯磺酰胺 在 sodium carbonate 、 potassium hydrogencarbonate 作用下， 以 水 、 丙酮 为溶剂， 生成 4-sulfamoyl-N-(3-morpholinopropyl)benzamide
  参考文献：
  名称：

  Three new aromatic sulfonamide inhibitors of carbonic anhydrases I, II, IV and XII

  摘要：

  4-Sulfamoyl-N-(3-morpholinopropyl)benzamide (I-1), N-(3-morpholinopropyl)benzene-1,4-disulfonamide (I-2) and N-(4-diethylaminoethoxybenzyl)benzene-1,4-bis(sulfonamide (I-3), were prepared and assayed as inhibitors of four carbonic anhydrase (CA) isoenzymes hCA I, hCA II, hCA IV and hCA XII. These compounds exhibited nanomolar half maximal inhibitory concentration (IC50) ranging from 58 to 740 nmol/L. All three aromatic sulfonamides show different activities for the isoenzymes studied with lowest affinity against isoenzyme hCA XII.

  DOI：

  10.3109/14756366.2011.649269

文献信息

• SUBSTITUTED SULPHONAMIDES, PROCESS FOR THEIR PREPARATION, PHARMACEUTICAL COMPOSITION COMPRISING THEREOF AND THEIR USE
  申请人：Gregan Fridrich

  公开号：US20100125076A1

  公开（公告）日：2010-05-20

  Substituted sulphonamides having the general formula (I) and salts, hydrates and solvates thereof were prepared and described, wherein R 1 is CO or SO 2 and R 2 is NH or O and where R represents linear or cyclic aliphatic chain and n represents number of linking aliphatic chain carbons (n can be 0, 1, 2 or 3), which are useful in the manufacture of the medicaments due to the carboanhydrase inhibition. These compounds are prepared by nucleophilic reaction of an amine with 4-sulfamoylbenzenesulphonyl chloride in the presence of triethylamine excess in tetrahydrofurane or in ether at temperature 0 to 20° C. The compounds show an antiglaucomatic activity.

  制备并描述了具有通式（I）及其盐、水合物和溶剂化合物的取代磺酰胺，其中R1为CO或SO2，R2为NH或O，R代表线性或环状脂肪链，n代表连接脂肪链碳数（n可以为0、1、2或3），由于碳酸酐酶抑制作用，这些化合物在药物制造中非常有用。这些化合物通过在四氢呋喃或醚中以0至20°C的温度下，在三乙胺过量存在下的氨与4-磺酰基苯磺酰氯的亲核反应制备而成。这些化合物表现出抗青光眼活性。
• SUBSITUTED SULPHONAMIDES, PROCESS FOR THEIR PREPARATION, PHARMACEUTICAL COMPOSITION COMPRISING THEREOF AND THEIR USE
  申请人：Unimed Pharma, Spol. S R.O.

  公开号：EP2142499A1

  公开（公告）日：2010-01-13
• Substituted sulphonamides, process for their preparation, pharmaceutical composition comprising thereof and their use for treating glaucoma
  申请人：Unimed Pharma, Spol. S R.O.

  公开号：EP2142499B1

  公开（公告）日：2014-12-10
• US8193184B2
  申请人：——

  公开号：US8193184B2

  公开（公告）日：2012-06-05
• [EN] SUBSITUTED SULPHONAMIDES, PROCESS FOR THEIR PREPARATION, PHARMACEUTICAL COMPOSITION COMPRISING THEREOF AND THEIR USE<br/>[FR] SULFAMIDES SUBSTITUÉS, LEUR PROCÉDÉ DE PRÉPARATION, COMPOSITION PHARMACEUTIQUE EN CONTENANT ET LEUR UTILISATION
  申请人：UNIMED PHARMA SPOL SRO

  公开号：WO2008130332A1

  公开（公告）日：2008-10-30

  [EN] Substituted sulphonamides having the general formula (I) and salts, hydrates and solvates thereof were prepared and described, wherein R¹ isCO or SO₂ and R² is NH or O and where R represents linear or cyclic aliphatic chain and n represents number of linking aliphatic chain carbons (n can be 0, 1, 2 or 3), which are useful in the manufacture of the medicaments due to the carboanhydrase inhibition. These compounds are prepared by nucleophilic reaction of an amine with 4-sulfamoylbenzenesulphonyl chloride in the presence of triethylamine excess in tetrahydrofurane or in ether at temperature 0 to 20 °C. The compounds show an antiglaucomatic activity.
  [FR] La présente invention concerne des sulfamides substitués de formule générale (I) et leurs sels, hydrates et solvates, où R¹ représente CO ou SO₂ et R² NH ou O et où R représente une chaîne aliphatique linéaire ou cyclique et n le nombre d'atomes de carbone de liaison de la chaîne aliphatique (n pouvant être égal à 0, 1, 2 ou 3), utilisables dans la fabrication de médicaments du fait de leur activité en matière d'inhibition de la carboanhydrase. Ces composés sont préparés par une réaction nucléophile entre une amine et du chlorure de sulfamoylbenzènesulfonyle en présence d'un excès de triéthylamine dans du tétrahydrofurane ou de l'éther à une température de 0 à 20 °C. Ces composés présentent une activité anti-glaucome.