2-nitro-4-dichloromethylsulfonylchlorobenzene | 61496-44-4

• 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: 2-nitro-4-dichloromethylsulfonylchlorobenzene
• 英文别名: 4-dichloromethylsulfonyl-2-nitrochlorobenzene；4-chloro-3-nitrophenyldichloromethyl sulfone；dichloromethyl 4-chloro-3-nitrophenylsulfone；Benzene, 1-chloro-4-[(dichloromethyl)sulfonyl]-2-nitro-；1-chloro-4-(dichloromethylsulfonyl)-2-nitrobenzene
• CAS: 61496-44-4
• 化学式: C₇H₄Cl₃NO₄S
• mdl: MFCD00607588
• 分子量: 304.538
• InChiKey: ALZIDDBBTJEMPS-UHFFFAOYSA-N

物化性质

• 熔点：
  92-93 °C(Solv: ethanol (64-17-5))
• 沸点：
  443.8±45.0 °C(Predicted)
• 密度：
  1.709±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 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：

  2-nitro-4-dichloromethylsulfonylchlorobenzene 在 盐酸 、 三乙胺 、 tin(ll) chloride 作用下， 以 苯 为溶剂， 反应 6.0h， 生成 2-amino-4-dichloromethylsulfonyl-N-cyclohexylaniline
  参考文献：
  名称：

  Ejmocki, Zdzislaw; Eckstein, Zygmunt; Gradon, Elzbieta, Polish Journal of Chemistry, 1983, vol. 57, # 7-9, p. 1037 - 1043

  摘要：

  DOI：
• 作为产物：
  描述：

  4-dichloromethylsulfonylchlorobenzene 在 硫酸 、 硝酸 作用下， 生成 2-nitro-4-dichloromethylsulfonylchlorobenzene
  参考文献：
  名称：

  5-卤代甲基磺酰基-苯并咪唑和苯并三唑衍生物的合成及体外抗菌活性

  摘要：

  合成了一系列5-卤代甲基磺酰基苯并咪唑和苯并三唑衍生物作为潜在的抗菌剂。开发了一种合成苯并咪唑的新方法。测试了这些化合物对一系列参考菌株和临床菌株的抗菌活性。参考菌株包括革兰氏阳性细菌（金黄色葡萄球菌，表皮葡萄球菌，枯草芽孢杆菌，蜡状芽孢杆菌，平邑酸杆菌，黄褐藻）和革兰氏阴性棒（大肠杆菌，寻常型毕赤酵母，铜绿假单胞菌） ，支气管败血波氏杆菌）。临床菌株包括6株耐甲氧西林（MRSA）和2株耐甲氧西林（MSSA）的金黄色葡萄球菌，1株耐甲氧西林的表皮葡萄球菌，3株粪肠球菌和2株粪肠球菌。在C-2位（4）具有三氟甲基取代基的化合物显示出与硝基呋喃妥因相当的显着抗菌活性，可对抗四种菌株，对黄褐微球菌的抗菌活性更高。临床葡萄球菌菌株（MRSA）的MIC值为12.5-25μg/ mL；对于肠球菌菌株，这些值为50-100μg/ mL。葡萄球菌和肠球菌组的参考菌株和临床菌株的MIC值分别相似。

  DOI：

  10.2174/1573406411309080015

文献信息

• Synthesis and Structural Characterization of Novel Trihalo-sulfone Inhibitors of WNK1
  作者：Melanie Rodriguez、Ashari Kannangara、Julita Chlebowicz、Radha Akella、Haixia He、Uttam K. Tambar、Elizabeth J. Goldsmith

  DOI：10.1021/acsmedchemlett.2c00216

  日期：2022.10.13

  inhibition of WNK1 using chemical synthesis and X-ray crystallography. Analogues that probed the role of specific functional groups to the inhibitory activity were synthesized. X-ray structures of trihalo-sulfone 1 and a second trihalo-sulfone 23 bound to WNK1 revealed active site binding to two of the three previously defined canonical inhibitor binding pockets as well as a novel binding site for the trihalo-sulfone

  不含赖氨酸 (K) [WNK] 激酶是结构独特的丝氨酸/苏氨酸蛋白激酶，具有血压调节和癌症的治疗潜力。通过高通量筛选鉴定出一类新型三卤砜化合物。Trihalo-sulfone 1成为 WNK1 的有效抑制剂，IC 50值为 1.6 μM。在此，我们使用化学合成和 X 射线晶体学定义了抑制 WNK1 所需的化学特征。合成了探索特定官能团对抑制活性的作用的类似物。与 WNK1 结合的三卤代砜1和第二个三卤代砜23的 X 射线结构揭示了与先前定义的三个典型抑制剂结合袋中的两个结合的活性位点以及三卤代砜部分的新结合位点。阐明这些新的相互作用位点可能有助于战略性设计更具选择性和更有效的 WNK 抑制剂。
• Ejmocki, Zdzislaw; Eckstein, Zygmunt; Krasinski, Pawel, Polish Journal of Chemistry, 1983, vol. 57, # 4/5/6, p. 555 - 560
  作者：Ejmocki, Zdzislaw、Eckstein, Zygmunt、Krasinski, Pawel、Zagorska, Krystyna

  DOI：——

  日期：——
• Gradon, Elzbieta; Ejmocki, Zdzislaw; Eckstein, Zygmunt, Polish Journal of Chemistry, 1981, vol. 55, # 2, p. 469 - 477
  作者：Gradon, Elzbieta、Ejmocki, Zdzislaw、Eckstein, Zygmunt

  DOI：——

  日期：——
• New synthetic sulfone derivatives inhibit growth, adhesion and the leucine arylamidase APE2 gene expression of Candida albicans in vitro
  作者：Monika Staniszewska、Małgorzata Bondaryk、Zbigniew Ochal

  DOI：10.1016/j.bmc.2014.11.038

  日期：2015.1

  The successful preventing and effective treatment of invasive Candida albicans infections required research focused on synthesis of new classes of agents and antifungal activity studies. Bromodichlorom-ethyl-4-chloro-3-nitrophenyl sulfone (named compound 6); dichloromethyl-4-chloro-3-nitrophenyl sulfone (named 7); and chlorodibromomethyl-4-hydrazino-3-nitrophenyl sulfone (named 11) on inhibition of planktonic cells' growth, leucine arylamidase APE2 gene expression, and adhesion to epithelial cells were investigated. In vitro anti-Candida activities were determined against wild-types, and the morphogenesis mutants: Delta efg1 and Delta cph1. MICs of compounds 6, 7 and 11 (concentrated at 0.25-16 mu g/ml) were determined using the Clinical and Laboratory Standards Institute Broth Microdilution Method (M27-A3 Document). APE2 expression was analyzed using RT-PCR; relative quantification was normalized against ACT1 in cells growth in YEPD and on Caco-2 cell line. Adherence assay of C. albicans to Caco-2 was performed in 24-well-plate.The structure activity relationship suggested that sulfone containing hydrazine function at C-1 (compound 11) showed higher antifungal activity (cell inhibition% = 100 at 1-16 mu g/ml) than the remaining sulfones with chlorine at C-1. Delta cph1/Delta efg1 was highly sensitive to compound 11, while the sensitivity was reduced in Delta cph1/Delta efg1:: EFG1 (% = 100 at 16-fold higher concentration). Compound 11 significantly affected adherence to epithelium (P <= 0.05) and hyphae formation. The APE2 up-regulation plays role in sulfones' resistance on MAP kinase pathway. Either CPH1 or EFG1 play a role in the resistance mechanism in sulfones. The strain-dependent phenomenon is a factor in the sulfone resistance mechanism. Sulfones' mode of action was attributed to reduced virulence arsenal in terms of adhesiveness and pathogenic potential related to the APE2 expression and morphogenesis. (C) 2014 Elsevier Ltd. All rights reserved.
• GRADON, E.;EJMOCKI, Z.;ECKSTEIN, Z., POL. J. CHEM., 1981, 55, N 2, 469-477
  作者：GRADON, E.、EJMOCKI, Z.、ECKSTEIN, Z.

  DOI：——

  日期：——