4--4'-nitrodiphenylsulphone | 111453-08-8

• 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--4'-nitrodiphenylsulphone
• 英文别名: 4-[N-(3-bromopropyl)-amino]-4'-nitrodiphenylsulphone；N-(3-bromopropyl)-4-(4-nitrophenyl)sulfonylaniline
• CAS: 111453-08-8
• 化学式: C₁₅H₁₅BrN₂O₄S
• 分子量: 399.265
• InChiKey: OMETZENLHSLUOL-UHFFFAOYSA-N

物化性质

• 沸点：
  586.2±45.0 °C(Predicted)
• 密度：
  1.563±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4--4'-nitrodiphenylsulphone 在 Raney Ni (W₂) 氢气 、 sodium 作用下， 以 甲醇 、 乙二醇甲醚 为溶剂， 50.0~60.0 ℃ 、500.0 kPa 条件下， 反应 9.33h， 生成 2,4-diamino-5-<4-<3-(4''-aminophenyl-4'-sulphonylphenylamino)propoxy>-3,5-dimethoxybenzyl>pyrimidine
  参考文献：
  名称：

  Synthesis of new 2,4-diamino-5-benzylpyrimidines active against various bacterial species

  摘要：

  New inhibitors of mycobacterial dihydrofolate reductase (DHFR) have been developed. These compounds show high inhibitory activities against Gram-negative and mycobacterial DHFR exceeding that for the commercially available DHFR blockers. Amongst these compounds K-130 shows a 100-fold lower MIC against M lufu than the most active derivatives known so far (TMP, BDP). Mycobacterium lufu was used as a model for the non cultivable strain M leprae. K-130 is also very active against other mycobacterial strains. Besides the higher affinity to the isolated enzyme, the increase in lipophilicity favours permeation of the mycobacterial cell wall and is responsible for the high inhibitory power of K-130 against mycobacteria. The lower activity against Gram-negative bacteria (E coli), despite high affinity to the enzyme, is explained by the hydrophilic nature of the outer score of the cell-wall components.

  DOI：

  10.1016/0223-5234(92)90007-n
• 作为产物：
  描述：

  4'-nitro-4-N-tosylaminodiphenyl sulfide 在 氢氧化钾 、 copper(l) iodide 、 硫酸 、 双氧水 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 7.0h， 生成 4--4'-nitrodiphenylsulphone
  参考文献：
  名称：

  Synthesis of new 2,4-diamino-5-benzylpyrimidines active against various bacterial species

  摘要：

  New inhibitors of mycobacterial dihydrofolate reductase (DHFR) have been developed. These compounds show high inhibitory activities against Gram-negative and mycobacterial DHFR exceeding that for the commercially available DHFR blockers. Amongst these compounds K-130 shows a 100-fold lower MIC against M lufu than the most active derivatives known so far (TMP, BDP). Mycobacterium lufu was used as a model for the non cultivable strain M leprae. K-130 is also very active against other mycobacterial strains. Besides the higher affinity to the isolated enzyme, the increase in lipophilicity favours permeation of the mycobacterial cell wall and is responsible for the high inhibitory power of K-130 against mycobacteria. The lower activity against Gram-negative bacteria (E coli), despite high affinity to the enzyme, is explained by the hydrophilic nature of the outer score of the cell-wall components.

  DOI：

  10.1016/0223-5234(92)90007-n

文献信息

• Substituted 2,4-diamino-5-benzylpyrimidines, their preparation and their
  申请人：Saarstickstoff-Fatol GmbH Chem.-Pharm. Fabrik

  公开号：US04912112A1

  公开（公告）日：1990-03-27

  Novel substituted 2,4-diamino-5-benzyl pyrimidines are described. The novel substances have antimicrobial activity and are particularly suitable for inhibiting the growth of mycobacteria. Combined with inhibitors such as diaminodiphenylsulphones, ring-substituted 4-aminodiphenylsulphones or ring and/or nitrogen-substituted diaminodiphenylsulphones, they have a marked synergistic activity.

  描述了新型替代的2,4-二氨基-5-苄基嘧啶类化合物。这些新型物质具有抗微生物活性，特别适用于抑制分枝杆菌的生长。与抑制剂如二氨基二苯砜、环替代的4-氨基二苯砜或环和/或氮替代的二氨基二苯砜结合，它们具有明显的协同作用。
• Substituierte 2,4-Diamino-5-benzylpyrimidine, deren Herstellung und deren Verwendung als Arzneimittel mit antimikrobieller Wirksamkeit
  申请人：Fatol Arzneimittel GmbH

  公开号：EP0231888A2

  公开（公告）日：1987-08-12

  Es werden neue substituierte 2,4-Diamino-5-benzylpyrimidine beschrieben. Die neuen Substanzen weisen antimikrobielle Wirksamkeit auf und sind insbesondere zur Hemmung des Wachstums von Mycobakterien geeignet. Sie entfalten in Kombination mit Hemmstoffen vom Typ der Diaminodiphenylsulfone, Ring-substituierten 4-Aminodiphenylsulfone oder Ring- und/oder Stickstoff-substituierten Diaminodiphenylsulfone ausgeprägte synergistische Wirksamkeit.

  本文介绍了新的取代型 2,4-二氨基-5-苄基嘧啶。 这些新物质具有抗菌活性，尤其适用于抑制分枝杆菌的生长。 与二氨基二苯砜、环取代的 4-氨基二苯砜或环和/或氮取代的二氨基二苯砜类型的抑制剂结合使用时，它们具有明显的协同活性。
• SEYDEL, JOACHIM K.;HALLER, ROLF;KANSY, MANFRED;HACHTEL, GERD
  作者：SEYDEL, JOACHIM K.、HALLER, ROLF、KANSY, MANFRED、HACHTEL, GERD

  DOI：——

  日期：——
• US4912112A
  申请人：——

  公开号：US4912112A

  公开（公告）日：1990-03-27