4-氨基苯-1,3-二磺酰胺 | 40642-90-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-氨基苯-1,3-二磺酰胺
• 中文别名: 氢氯噻嗪杂质28
• 英文名称: 4-amino-1,3-benzenedisulfonamide
• 英文别名: 4-amino-benzene-1,3-disulfonic acid diamide；4-Amino-benzol-1,3-disulfonsaeure-diamid；4-Aminobenzene-1,3-disulfonamide
• CAS: 40642-90-8
• 化学式: C₆H₉N₃O₄S₂
• 分子量: 251.287
• InChiKey: BOZSDDFQWJUBNG-UHFFFAOYSA-N

物化性质

• 熔点：
  230-231.5 °C
• 沸点：
  594.8±60.0 °C(Predicted)
• 密度：
  1.679±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  163
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-氨基苯-1,3-二磺酰胺 、 天然芥菜籽油 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 4-(3-Allyl-thioureido)-benzene-1,3-disulfonic acid diamide
  参考文献：
  名称：

  Carbonic anhydrase inhibitors - Part 49: Synthesis of substituted ureido and thioureido derivatives of aromatic/heterocyclic sulfonamides with increased affinities for isozyme I

  摘要：

  Reaction of nine aromatic/heterocyclic sulfonamides containing a free amino group with aryl isocyanates/isothiocyanates or allyl isothiocyanate afforded the corresponding urea/thiourea derivatives, which were characterized by standard physico-chemical procedures and assayed as inhibitors of three isozymes of carbonic anhydrase (CA), i.e. hCA I, hCA II and bCA IV (h = human, b = bovine isozyme). Another series of compounds, 1,5-disubstituted-2-thiobiuret derivatives, were prepared by reaction of 3,4-dichlorophenyl isocyanate with thioureido-containing aromatic/heterocyclic sulfonamides. Good inhibition of all these three CA isozymes was observed with the new compounds, but an exciting finding was that the ureas/thioureas and especially the above-mentioned thiobiurets reported here have an increased affinity to the slow isozyme hCA I, generally less susceptible to inhibition by sulfonamides, as compared to the rapid isozymes hCA II and bCA IV. Some of the new compounds might constitute good lead molecules for developing more selective CA I inhibitors. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(98)80033-0
• 作为产物：
  描述：

  4-氨基-5-氯苯-1,3-二磺酰胺 在 palladium on activated charcoal sodium hydroxide 、 氢气 作用下， 生成 4-氨基苯-1,3-二磺酰胺
  参考文献：
  名称：

  Diuretics: Aminobenzenedisulfonamides

  摘要：

  DOI：

  10.1021/jo01076a027

文献信息

• Novel compounds and their use as positive AMPA receptor modulators
  申请人：Neurosearch A/S.

  公开号：US20040043987A1

  公开（公告）日：2004-03-04

  The invention provides novel compounds represented by the general formula 5 compound represented by the formula: 1 wherein the bond represented by the broken line may be a single, a double bond or absent; and if the bond is absent, then the nitrogen is substituted with a hydrogen and R 2 ; X represents SO 2 or C═O or CH 2 ; Y represents —CH(R 4 )—, —N(R 4 )— or —N(R 4 )—CH 2 —, O; and the meaning of R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 are as defined in the application The compounds are useful as positive modulators of the AMPA-receptor.

  该发明提供了一种新型化合物，其通式5的化合物如下所示：其中由虚线表示的键可以是单键、双键或不存在；如果键不存在，则氮原子用氢和R2取代；X代表SO2或C═O或CH2；Y代表—CH(R4)—、—N(R4)—或—N(R4)—CH2—、O；R2、R3、R4、R5、R6、R7和R8的含义如申请中所定义。这些化合物可用作AMPA受体的阳性调节剂。
• Photolytic Decomposition of Hydrochlorothiazide
  作者：Swasono R. Tamat、Douglas E. Moore

  DOI：10.1002/jps.2600720221

  日期：1983.2

  Hydrochlorothiazide decomposes upon irradiation with near-UV light (lambda greater than 310 nm) both in methanol and aqueous solutions. In the photolysis the chlorine substituent is removed to be replaced by either--H or--OR from the solvent ROH. Hydrolysis of the thiadiazine ring is superimposed upon the dechlorination. The presence of oxygen inhibits the decomposition. The mechanism of the photolysis

  氢氯噻嗪在甲醇和水溶液中均受到近紫外光（λ大于310 nm）照射后分解。在光解过程中，氯取代基被去除，被溶剂ROH中的-H或-OR取代。噻二嗪环的水解与脱氯作用叠加。氧的存在抑制了分解。建议光解的机理涉及阳离子自由基的形成，这有助于水解步骤。5-氯-2,4-二磺酰胺基苯胺（一种氢氯噻嗪的正常水解产物）也易于通过类似的机理进行光解脱氯。
• Compounds and their use as positive AMPA receptor modulators
  申请人：NeuroSearch A/S

  公开号：US07235548B2

  公开（公告）日：2007-06-26

  The invention provides novel compounds represented by the general formula compound represented by the formula: wherein the bond represented by the broken line may be a single, a double bond or absent; and if the bond is absent, then the nitrogen is substituted with a hydrogen and R2; X represents SO2 or C═O or CH2; Y represents —CH(R4)—, —N(R4)— or —N(R4)—CH2—, O; and the meaning of R2, R3, R4, R5, R6, R7, and R8 are as defined in the application The compounds are useful as positive modulators of the AMPA-receptor.

  本发明提供了由一般式化合物表示的新化合物，该一般式化合物由以下式子表示：其中，由断线表示的键可以是单键、双键或不存在；如果键不存在，则氮被氢和R2取代；X代表SO2、C═O或CH2；Y代表—CH(R4)—、—N(R4)—或—N(R4)—CH2—、O；而R2、R3、R4、R5、R6、R7和R8的含义如申请书中所定义。这些化合物可用作AMPA受体的正向调节剂。
• SUBSTITUTED N-AMINOMETHYLENE SULFONAMIDES, PRODUCTION AND USE THEREOF AS MEDICAMENTS
  申请人：SCHOENAFINGER Karl

  公开号：US20080069851A1

  公开（公告）日：2008-03-20

  Disclosed are compounds of the general formula (I), with the definitions of the substituents R 1 to R 5 , A and X being detailed in the text, and to their physiologically tolerated salts, to processes for preparing these compounds and to the use thereof as inhibitors of hormone-sensitive lipase (HSL).

  本发明揭示了一般式（I）的化合物，其中定义了取代基R1到R5，A和X的详细信息，以及其生理耐受盐的制备过程，以及它们作为激素敏感性脂肪酶（HSL）抑制剂的用途。
• Identification of Chlorothiazide and Hydrochlorothiazide UV-A Photolytic Decomposition Products
  作者：Larry K. Revelle、Steven M. Musser、Bradley J. Rowe、Irina C. Feldman

  DOI：10.1021/js9601501

  日期：1997.5

  chromatography. The standards were characterized by high resolution fast atom bombardment MS and 1H NMR. The photolysis of chlorothiazide resulted in photodehalogenation products exclusively, while the irradiation of hydrochlorothiazide primarily yielded photodehalogenation products with significant yields of photodehydrogenation products and minor amounts of thermal hydrolysis products.

  为了模拟在正常条件下的降解，用荧光UV-A灯照射氢氯噻嗪和氯噻嗪的甲醇溶液。通过与以电喷雾电离质谱，紫外光谱和高效液相色谱为特色的合成标准品进行比较，确定了降解产物。这些标准品的特征在于高分辨率快速原子轰击质谱和1H NMR。氯噻嗪的光解仅产生光脱卤产物，而氢氯噻嗪的辐射主要产生光脱卤产物，其中光脱氢产物的产率很高，而热水解产物的量很少。