potassium 4-chloro-3,5-dinitrobenzenesulfonate | 38185-06-7

• 物质功能分类: 化学试剂 - 有机试剂 - 磺酸盐/亚磺酸盐
• 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: potassium 4-chloro-3,5-dinitrobenzenesulfonate
• 英文别名: potassium;4-chloro-3,5-dinitrobenzenesulfonate
• CAS: 38185-06-7
• 化学式: C₆H₂ClN₂O₇S*K
• 分子量: 320.708
• InChiKey: SOKIKHRZBYSIFN-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.94
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  157
• 氢给体数：
  0
• 氢受体数：
  7

安全信息

• 海关编码：
  2904909090

制备方法与用途

用途：用作农药中间体

反应信息

• 作为反应物：
  描述：

  potassium 4-chloro-3,5-dinitrobenzenesulfonate 在 五氯化磷 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 4-dipropylamino-N-methyl-3,5-dinitrobenzenesulfonamide
  参考文献：
  名称：

  Synthesis and Antitubulin Activity of N- and N⁴-Substituted 3,5-Dinitro Sulfanilamides against African Trypanosomes and Leishmania

  摘要：

  Thirty analogues of N-1-phenyl-3,5-dinitro-N-4,N-4-di-n-propylsulfanilamide (GB-II-5, compound 3), a new antikinetoplastid antimitotic agent, have been synthesized and evaluated. The addition of simple functional groups to the N1 aromatic ring generally decreases antiparasitic and antimitotic potency, but placement of a dibutyl substituent at the N4 nitrogen to give N-1-phenyl-3,5-dinitro-N-4,N-4-di-n-butylsulfanilamide (compound 35) augments antitrypanosomal and antileishmanial activity. Compound 35 possesses IC50 values of 0.12 and 2.6 muM against cultured T. brucei and L. donovani amastigote-like forms, surpassing the activity of compound 3 against these parasites by 3.4- and 1.9-fold, respectively. Compound 35 inhibits the assembly of leishmanial tubulin with an IC50 of 6.9 muM and displays antimitotic effects in cultured T brucei as assessed by flow cytometry, but shows little effect on purified mammalian tubulin, and displays 100-fold selectivity for trypanosomes over two mammalian cell lines. Although 3 and 35 were not effective in initial in vivo antitrypanosomal assays, the in vitro potency and ;selectivity of these compounds make N-1-aryl-3,5-dinitro-N-4,N-4-dialkylsulfanilamides a promising new class of antikinetoplastid agents that act on parasite tubulin.

  DOI：

  10.1021/jm0304461
• 作为产物：
  描述：

  氯苯 在 硫酸 、 potassium nitrate 作用下， 生成 potassium 4-chloro-3,5-dinitrobenzenesulfonate
  参考文献：
  名称：

  Synthesis of SMZ derivatives and investigation of effects on germination, root,and plant growth ofArabidopsis thalianaL.

  摘要：

  在不同的取代反应条件下，通过与含有苯磺酰氯和苯胺衍生物的各种官能团反应，合成了一系列磺酰胺衍生物。通过熔点、傅立叶变换红外光谱、^{1}$H NMR、^{13}$C NMR 和 LC-MS/MS 技术确认了 SMZ 衍生物的结构。为了研究这些衍生物的细胞毒性作用，我们使用了一种模式植物物种。将合成的化合物（S1-S5）和作为阳性对照的磺胺二甲嘧啶（SMZ）应用于拟南芥种子。结果表明，S3 和 S4 会导致植物根系变短，湿重降低。用 S2 和 S5 处理的植物与未处理的对照组相似，对生长没有影响，而 S1 则略微减少了根的长度和湿重。这些结果表明，S3 和新合成的 S4 衍生物有可能用作除草剂，因为它们对大丽花植物具有细胞毒性作用。

  DOI：

  10.3906/kim-1901-27

文献信息

• Synthesis and Biological Evaluation of Some Novel N-Alkyl/Aryl-1-Nitro-10H-Phenothiazine-3-Sulfonamide Derivatives
  作者：Vasudha Mallam、M. Ranadheer Kumar、Baru Vijaya Kumar

  DOI：10.1134/s1068162021060170

  日期：2021.11

  series of new derivatives of N-alkyl/aryl-1-nitro-10H-phenothiazine-3-sulfonamides were developed and synthesized by 1-nitro-10H-phenothiazine-3-sulfonyl chloride with various amines. The intermediates 1-nitro-10H-phenothiazine-3-potassium sulfonate and 1-nitro -10H-phenothiazine-3-sulfonyl chlorides were synthesized by well known methods. The newly synthesized compounds were evaluated for their antioxidant

  摘要 一系列新衍生物的ñ -烷基/芳基-1-硝基- 10 ħ -吩噻嗪-3-磺酰胺进行了开发和由1-硝基10中合成ħ -吩噻嗪-3-磺酰氯与各种胺。中间体1-硝基10 ħ -吩噻嗪-3-磺酸钾和1-硝基-10 ħ -吩噻嗪-3-磺酰氯可通过熟知的方法合成。评估了新合成的化合物的抗氧化和抗菌活性，1-硝基-N- (噻吩-2-基甲基)-10 H-吩噻嗪-3-磺酰胺，N- (2-氯苯基)-1-硝基-10 H -phenothiazine-3-sulfonamide 和N发现 -cyclohexyl -1-nitro-10 H -phenothiazine-3-sulfonamide 与标准药物相比表现出良好至极好的活性。
• Aromatic diamines containing sulfonic acid aryl esters, a process for
  申请人：Bayer Aktiengesellschaft

  公开号：US04797427A1

  公开（公告）日：1989-01-10

  The present invention is directed to new aromatic diamines containing sulfonic acid aryl esters corresponding to the formula ##STR1## wherein R.sub.1 represents hydrogen, an optionally branched C.sub.1 -C.sub.6 alkyl radical (preferably a methyl group), a C.sub.1 -C.sub.6 alkoxy radical or a halogen atom (preferably chlorine) and R.sub.2 and R.sub.3 which may be the same or different, represent hydrogen, an optionally branched C.sub.1 -C.sub.20 (preferably C.sub.1 -C.sub.6) alkyl radical, a C.sub.1 -C.sub.6 alkoxy radical or a halogen atom (preferably chlorine). The present invention is also directed to a process for the production of the above aromatic diamines containing sulfonic acid esters by the reaction of optionally substituted sulfochlorides with optionally substituted phenols followed by hydrogenation. Finally, the present invention is directed to the use of aromatic diamines containing sulfonic acid aryl esters as a synthesis component for the production of polyurethane plastics by the isocyanate polyaddition process.

  本发明涉及一种新的芳香族二胺，其含有对应于以下式子的磺酸芳基酯：##STR1##其中R.sub.1代表氢，可选的支链C.sub.1-C.sub.6烷基基团（优选为甲基基团），C.sub.1-C.sub.6烷氧基基团或卤素原子（优选为氯）；R.sub.2和R.sub.3可以相同也可以不同，代表氢，可选的支链C.sub.1-C.sub.20（优选为C.sub.1-C.sub.6）烷基基团，C.sub.1-C.sub.6烷氧基基团或卤素原子（优选为氯）。本发明还涉及一种通过将可选的取代磺酰氯与可选的取代苯酚反应后进行氢化制备上述含有磺酸酯的芳香族二胺的方法。最后，本发明还涉及将含有磺酸芳基酯的芳香族二胺用作异氰酸酯聚加成法生产聚氨酯塑料的合成组分。
• Development of a novel high-throughput screen for the identification of new inhibitors of protein S-acylation
  作者：Christine Salaun、Hiroya Takizawa、Alex Galindo、Kevin R. Munro、Jayde McLellan、Isamu Sugimoto、Tomotaka Okino、Nicholas C.O. Tomkinson、Luke H. Chamberlain

  DOI：10.1016/j.jbc.2022.102469

  日期：2022.10

  either for use as tool compounds or for potential development for therapeutic purposes. Here, we developed and implemented a novel FRET-based high-throughput assay for the discovery of compounds that interfere with autoacylation of zDHHC2, an enzyme that is implicated in neuronal S-acylation pathways. Our screen of >350,000 compounds identified two related tetrazole-containing compounds (TTZ-1 and TTZ-2)

  蛋白质 S-酰化是一种可逆的翻译后修饰，可调节许多细胞蛋白质的定位和功能。S-酰化由锌指 DHHC (Asp-His-His-Cys) 结构域 (zDHHC) 蛋白家族介导，该蛋白由 23 种不同的ZDHHC编码人类基因组中的基因。这些酶通过两步过程催化 S-酰化，涉及催化 DHHC 基序中半胱氨酸残基的“自动酰化”，然后将酰基链转移至底物半胱氨酸。S-酰化对于许多基本生理过程至关重要，并且人们越来越关注 zDHHC 酶作为一系列疾病的新型药物靶点。然而，目前缺乏 S-酰化的化学调节剂，既可用作工具化合物，也可用于治疗目的的潜在开发。在这里，我们开发并实施了一种基于 FRET 的新型高通量测定法，用于发现干扰 zDHHC2 自动酰化的化合物，zDHHC2 是一种与神经元 S-酰化途径有关的酶。我们的屏幕>350，000 种化合物鉴定出两种相关的含四唑化合物（TTZ-1 和 TTZ-2），它们在无细胞系统中抑制
• Synthesis and Biological Evaluation of Fused Imidazo[4,5,1-kl]phenothiazine-4-sulfonamides as Potent Antibacterial and Anticancer Agents
  作者：Vasudha Mallam、Vijayakumar Allam、G. Brahmeshwari

  DOI：10.1134/s1068162023060183

  日期：2023.11

  Abstract In the present study, a novel series of fused imidazole derivatives containing phenothiazine-sulfonamide were synthesized and screened for their antibacterial and anticancer activity. Among all the compounds synthesized, 1-(3-bromophenyl)imidazo[4,5,1-kl]phenothiazine-4-sulfonamide and 1-(2-chlorophenyl)imidazo[4,5,1-kl]phenothiazine-4-sulfonamide showed excellent inhibition against B. subtilis

  摘要 在本研究中，合成了一系列新型含有吩噻嗪磺酰胺的稠合咪唑衍生物，并筛选了其抗菌和抗癌活性。在所有合成的化合物中，1-(3-溴苯基)咪唑并[4,5,1-kl]吩噻嗪-4-磺酰胺和1-(2-氯苯基)咪唑[4,5,1-kl]吩噻嗪-4-磺酰胺对枯草芽孢杆菌和金黄色葡萄球菌菌株表现出优异的抑制作用，MIC 值为 3.12 和 6.25 µg/mL。与标准链霉素相比，其余化合物对所有测试菌株均表现出中度至低度的活性。类似地，化合物1-(4-羟基-3-甲氧基苯基)咪唑并[4,5,1-kl]吩噻嗪-4-磺酰胺和1-(4-羟基苯基)咪唑并[4,5,1-kl]吩噻嗪-4 -磺酰胺对 MCF-7 和 HeLa 细胞系表现出良好的抗癌活性。其余化合物对测试的癌细胞系表现出较差的活性。
• Antikinetoplastid antimitotic activity and metabolic stability of dinitroaniline sulfonamides and benzamides
  作者：Tesmol G. George、Jayaseharan Johnsamuel、Dawn A. Delfín、Adam Yakovich、Mitali Mukherjee、Mitch A. Phelps、James T. Dalton、Dan L. Sackett、Marcel Kaiser、Reto Brun、Karl A. Werbovetz

  DOI：10.1016/j.bmc.2006.04.017

  日期：2006.8

  N-1-Phenyl-3,5-dinitro-N-4,N-4-di-n-propylsulfanilamide (1) and N-1-phenyl-3,5-dinitro-N-4,N-4-di-n-butylsulfanilamide (2) show potent in vitro antimitotic activity against kinetoplastid parasites but display poor in vivo activity. Seventeen new dinitroaniline sulfonamide and eleven new benzamide analogs of these leads are reported here. Nine of the sulfonamides display in vitro IC50 values under 500 nM against African trypanosomes, and the most active antikinetoplastid compounds also inhibit the in vitro assembly of purified leishmanial tubulin with potencies similar to that of 2. While several of the potent compounds are rapidly degraded by rat liver S9 fractions in vitro, N-1-(3-hydroxy)phenyl-3,5-dinitro-N-4,N-4-di-n-butylsulfanilamide (21) displays an IC50 value of 260 nM against African trypanosomes in vitro and is more stable than 2 in the in vitro metabolism assay. (c) 2006 Elsevier Ltd. All rights reserved.