(4-bromomethyl-phenyl)-(4-nitro-phenyl)-sulfone | 100398-04-7

• 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-bromomethyl-phenyl)-(4-nitro-phenyl)-sulfone
• 英文别名: (4-Brommethyl-phenyl)-(4-nitro-phenyl)-sulfon；4-bromomethyl-4'-nitrodiphenylsulphone；Benzene, 1-(bromomethyl)-4-[(4-nitrophenyl)sulfonyl]-；1-(bromomethyl)-4-(4-nitrophenyl)sulfonylbenzene
• CAS: 100398-04-7
• 化学式: C₁₃H₁₀BrNO₄S
• 分子量: 356.197
• InChiKey: BOCHNTFSFIEKPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  88.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4-bromomethyl-phenyl)-(4-nitro-phenyl)-sulfone 在 Raney Ni (W₂) 氢气 、 sodium methylate 作用下， 以 甲醇 、 乙二醇甲醚 为溶剂， 25.0~50.0 ℃ 、500.0 kPa 条件下， 反应 1.33h， 生成 5-[[4-[[4-(4-Aminophenyl)sulfonylphenyl]methoxy]-3-methoxyphenyl]methyl]pyrimidine-2,4-diamine
  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-[(4-硝基苯基)硫代]甲苯 在 双氧水 、 溴 、 溶剂黄146 作用下， 生成 (4-bromomethyl-phenyl)-(4-nitro-phenyl)-sulfone
  参考文献：
  名称：

  292.氨基酸系列的抑菌作用。第二部分 丙氨酸衍生物的进一步研究

  摘要：

  DOI：

  10.1039/jr9490001374

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。
• Crystal-structure-based design and synthesis of benz[cd]indole-containing inhibitors of thymidylate synthase
  作者：Michael D. Varney、Gifford P. Marzoni、Cindy L. Palmer、Judith G. Deal、Stephanie Webber、Katherine M. Welsh、Russell J. Bacquet、Charlotte A. Bartlett、Catharine A. Morse

  DOI：10.1021/jm00082a006

  日期：1992.2

  The X-ray crystal-structure-based design, synthesis, and biological activity of a novel family of benz[cd]indole-containing inhibitors of thymidylate synthase (TS) are described. The structure-activity of the lead compound was studied by conceptually dividing the molecule into four regions and independently optimizing the substituents for each region. Combination of favored substituents for each region led to inhibitors with K(i)'s against the human enyzme in the range of 10-20 nM. Thymidine shift experiments suggested that the cytotoxic properties of the best enzyme inhibitors were due to TS targeting in cells. The inhibitors were synthesized from substitued 6-aminobenz[cd]indol-2(1H)-ones by alkylation with both a simple alkyl group and a substituted benzylic portion. The 2,6-diaminobenz[cd]indoles were prepared from the corresponding lactams by conversion to the thiolactam, alkylation to the methylated thiolactam, and then displacement with a substituted or unsubstituted amine.
• 4-Aminomethyl-4'-aminodiphenylsulfone and Related Compounds^*
  作者：WILHELM WENNER

  DOI：10.1021/jo01362a050

  日期：1957.11
• US4912112A
  申请人：——

  公开号：US4912112A

  公开（公告）日：1990-03-27
• [EN] ANTIFOLATE QUINAZOLINES
  申请人：AGOURON PHARMACEUTICALS, INC.

  公开号：WO1993013079A1

  公开（公告）日：1993-07-08

  (EN) The present invention relates to certain quinazoline compounds capable of inhibiting folate metabolic pathways, to pharmaceutical compositions containing these compounds, and to the use of these compounds to inhibit folate metabolic pathways, including all effects derived from the inhibition of folate metabolic pathways. Effects derived from the inhibition of folate metabolic pathways include the inhibition of the growth and proliferation of the cells of higher organisms and microorganisms, such as bacteria, yeasts and fungi. Such effects may include the inhibition of the enzymes thymidylate synthase or dihydrofolate reductase, or both. A process for preparing the quinazoline antifolate compounds according to the present invention is also disclosed.(FR) On décrit certains composés de quinazoline pouvant inhiber les voies métaboliques des folates, des compositions pharmaceutiques les contenant, et leur utilisation dans l'inhibition des voies métaboliques des folates, notamment tous les effets dérivés de l'inhibition des voies métaboliques des folates. Les effets dérivés de l'inhibition des voies métaboliques des folates sont notamment l'inhibition de la croissance et de la prolifération des cellules des organismes supérieurs et des microorganismes, par exemple les bactéries, les levures et les champignons. Ces effets comprennent éventuellement l'inhibition des enzymes thymidylate-synthase et/ou dihydrofolate-réductase. On a également prévu un procédé de préparation de ces composés anti-folates de quinazoline.