N-ethyl-N-methylsulfonanilide | 51323-67-2

• 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: N-ethyl-N-methylsulfonanilide
• 英文别名: N-ethyl-methanesulfonanilide；Methansulfonsaeure-aethylanilid；N-Aethyl-methansulfonanilid；N-ethyl-N-phenylmethanesulfonamide
• CAS: 51323-67-2
• 化学式: C₉H₁₃NO₂S
• mdl: MFCD00584471
• 分子量: 199.274
• InChiKey: MFRPSQUJLQLXJD-UHFFFAOYSA-N

物化性质

• 沸点：
  299.2±23.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-ethyl-N-methylsulfonanilide 在 三甲基氯硅烷 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以84%的产率得到N-乙基苯胺
  参考文献：
  名称：

  Deprotection of sulfonamides using iodotrimethylsilane

  摘要：

  The deprotection of sulfonamides is achieved under neutral conditions by reaction with iodotrimethylsilane in acetonitrile at reflux. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02646-x
• 作为产物：
  描述：

  苯胺 在 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 N-ethyl-N-methylsulfonanilide
  参考文献：
  名称：

  由静电相互作用引导的空间偏置和无偏置衬底的元选择性 C-H 硼酸化

  摘要：

  描述了空间偏压和无偏压底物的静电定向代谢硼化。硼酸化遵循配体和底物之间部分正电荷和负电荷之间的静电相互作用。使用这种策略，已经证明大量具有挑战性的底物，尤其是 4 取代底物，可以在间位选择性地硼酸化。此外，未取代的底物也表现出优异的间位选择性。该反应采用实验室稳定的配体并在较温和的温度下进行，无需合成庞大而复杂的配体/模板。

  DOI：

  10.1021/jacs.1c01770

文献信息

• Synthesis and aldose reductase inhibitory activities of novel N -nitromethylsulfonanilide derivatives
  作者：Jun Inoue、Ying-She Cui、Osamu Sakai、Yoshikuni Nakamura、Hiromi Kogiso、Peter F Kador

  DOI：10.1016/s0968-0896(00)00158-9

  日期：2000.8

  A novel series of 14 N-nitromethylsulfonanilide derivatives were synthesized and evaluated for their ability to inhibit recombinant aldose reductase. Computational docking simulations provided a good explanation for the observed structure-activity relationships. Kinetic analysis of (2-fluoro-5-methyl-N-methyl)-N-nitromethylsulfonanilide, 11, one of the most potent compounds in this series with an IC50

  合成了一系列新的14种N-硝基甲基磺酰苯胺衍生物，并评估了它们抑制重组醛糖还原酶的能力。计算对接模拟为观察到的结构-活性关系提供了很好的解释。动力学分析（2-氟-5-甲基-N-甲基）-N-硝基甲基磺酰苯胺，该系列中最有效的化合物之一，IC50 = 0.35 M，显示出无竞争性的抑制作用。随后用11种大鼠晶状体进行的体外培养研究表明，该系列醛糖还原酶抑制剂可有效预防或延缓与糖尿病有关的糖性白内障形成。
• 1-(sulfonyl)-5-(arylsulfonyl)indoline as activators of the tumor cell specific M2 isoform of pyruvate kinase
  作者：Avihai Yacovan、Rachel Ozeri、Tzofit Kehat、Sima Mirilashvili、Daniel Sherman、Alex Aizikovich、Alina Shitrit、Efrat Ben-Zeev、Nili Schutz、Osnat Bohana-Kashtan、Alexander Konson、Vered Behar、Oren M. Becker

  DOI：10.1016/j.bmcl.2012.08.054

  日期：2012.10

  describe the discovery and optimization of a series of PKM2 activators derived from the 2-((2,3-dihydrobenzo[b][1,4] dioxin-6-yl)thio)-1-(2-methyl-1-(methylsulfonyl)indolin-5-yl) ethanone scaffold. The synthesis, SAR analysis, enzyme active site docking, enzymatic reaction kinetics, selectivity and pharmaceutical properties are discussed.

  癌细胞优先使用糖酵解而不是氧化磷酸化来快速生长。即使氧气充足，它们也会消耗大量的葡萄糖来产生乳酸，这种现象被称为沃伯格效应。这种代谢变化源自糖酵解丙酮酸激酶（PK）的其他剪接同工型的表达从PKM1到PKM2的转变。当PKM1具有组成型活性时，PKM2通过小分子活化剂从无活性的二聚体形式转换为有活性的四聚体形式。相对于许多正常细胞中PKM1的流行率，PKM2在癌细胞中的流行率表明了一种治疗策略，其中PKM2的激活可能抵消癌细胞中异常的细胞代谢，从而降低了细胞的增殖。在这里，我们描述了从2-（（2,3-dihydrobenzo [b] [1,4]二恶英-6-基）硫基）-1-（2-甲基-1）衍生的一系列PKM2激活剂的发现和优化。 -（甲基磺酰基）吲哚-5-基）乙酮支架。讨论了合成，SAR分析，酶活性位点对接，酶促反应动力学，选择性和药物性质。
• Irreversible HIV protease inhibitors, compositions containing same and process for the preparation thereof
  申请人：LG Chemical Limited

  公开号：EP0812857A1

  公开（公告）日：1997-12-17

  The present invention relates to novel compounds of formula (I) which have inhibitory activity against human immunodeficiency virus ("HIV") protease, a process for the preparation thereof, and compositions for prevention or treatment of AIDS by HIV infection comprising the above compounds as active ingredients. wherein: R1 is an aromatic group, a nitrogen-containing aromatic group, C1-4 alkyl group optionally substituted with an aromatic group or a nitrogen-containing aromatic group, C1-4 alkoxy group optionally substituted with an aromatic group or a nitrogen-containing aromatic group; R2 is an amino acid residue or a C1-8 alkyl group substituted with a C1-4 alkylsulfonyl group; R3 is a C1-4 alkyl group optionally substituted with an aromatic group; R4 is hydrogen or a C1-4 alkyl group; R5 is an aromatic group, a C1-10 alkyl group or a C1-4 alkyl groups optionally substituted with an aromatic group; and n is 1 or 2.

  本发明涉及一种具有对人类免疫缺陷病毒（“HIV”）蛋白酶抑制活性的新化合物（I）的公式，以及其制备过程和包含上述化合物作为活性成分的用于预防或治疗艾滋病的组合物。其中：R1是芳香基，含氮芳香基，C1-4烷基（可选地取代芳香基或含氮芳香基），C1-4烷氧基（可选地取代芳香基或含氮芳香基）；R2是氨基酸残基或C1-8烷基（取代有C1-4烷基磺酰基）；R3是C1-4烷基（可选地取代芳香基）；R4是氢或C1-4烷基；R5是芳香基，C1-10烷基或C1-4烷基（可选地取代芳香基）；n为1或2。
• Irreversible HIV protease inhibitors, compositions containing same and
  申请人：LG Chemical Limited

  公开号：US05679687A1

  公开（公告）日：1997-10-21

  The present invention relates to novel compounds of formula (I) which have inhibitory activity against human immunodeficiency virus ("HIV") protease, a process for the preparation thereof, and compositions for prevention or treatment of AIDS by HIV infection comprising the above compounds as active ingredients. ##STR1## wherein: R.sup.1 is an aromatic group, a nitrogen-containing aromatic group, C.sub.1-4 alkyl group optionally substituted with an aromatic group or a nitrogen-containing aromatic group, C.sub.1-4 alkoxy group optionally substituted with an aromatic group or a nitrogen-containing aromatic group; R.sup.2 is an amino acid residue or a C.sub.1-8 alkyl group substituted with a C.sub.1-4 alkylsulfonyl group; R.sup.3 is a C.sub.1-4 alkyl group optionally substituted with an aromatic group; R.sup.4 is hydrogen or a C.sub.1-4 alkyl group; R.sup.5 is an aromatic group, a C.sub.1-10 alkyl group or a C.sub.1-4 alkyl groups optionally substituted with an aromatic group; and n is 1 or 2.

  本发明涉及具有对人类免疫缺陷病毒（“HIV”）蛋白酶具有抑制活性的化合物的新型化合物（I）的公式，其制备方法以及包含上述化合物作为活性成分的用于预防或治疗艾滋病的组合物。其中：R.sup.1是芳香基，含氮芳香基，C.sub.1-4烷基，可选择地取代为芳香基或含氮芳香基，可选择地取代为芳香基或含氮芳香基的C.sub.1-4烷氧基；R.sup.2是氨基酸残基或取代有C.sub.1-4烷基磺酰基的C.sub.1-8烷基；R.sup.3是可选择地取代为芳香基的C.sub.1-4烷基；R.sup.4是氢或C.sub.1-4烷基；R.sup.5是芳香基，C.sub.1-10烷基或可选择地取代为芳香基的C.sub.1-4烷基；n为1或2。
• DERIVATIVES OF 2-PYRIDIN-2-YL-PYRAZOL-3(2H)-ONE, PREPARATION AND THERAPEUTIC USE THEREOF
  申请人：ALTENBURGER Jean-Michel

  公开号：US20110301148A1

  公开（公告）日：2011-12-08

  The invention relates to compounds corresponding to formula (I), in the form of the base or of an acid-addition salt: in which n is equal to 0, 1, 2, 3 or 4; m is equal to 0, 1 or 2; o is equal to 0 or 1; X represents a group —CH 2 , —CH(R′)—, —NH(R′)— or a heteroatom chosen from O and S, it being understood that R′ represents a group —(C1-C5)alkyl, —(C1-C5)alkoxy, —CH 2 -aryl, —C(O)R5 or —COOR5; R1 represents an oxo group, —COOR5, —W—OH or —W—NR5R6; R2 represents an H atom or a group chosen from the groups (i) —(C1-C5)alkyl, (ii) —(C1-C5)alkoxy, (iii) —COOR5, (iv) —NR5R6, (v) —C(O)—NR5R6, (vi) —SO 2 —NR3R4, (vii) heteroaryl optionally substituted with a group —(C1-C5)alkyl, (viii) —W-aryl, (ix) —W-heteroaryl, (x) —O—W-aryl, (xi) —O—W-heteroaryl and (xii) —O—W—NR5R6; it being understood that R3 and R4, (i) which may be identical or different, represent, independently of each other, an H atom, a group —(C1-C5)alkyl, —(C3-C6)cycloalkyl, aryl, heteroaryl, —CH 2 -heteroaryl, —(C1-C5)alkyl-NR5R6, —W—OH or —W—NR5R6; or (ii) form, together with the nitrogen atom that bears them, a heterocycloalkyl group optionally substituted with one or more groups chosen from the groups —(C1-C5)alkyl and —CH 2 -aryl; W is a group —(C1-C5)alkylene, optionally substituted with one or more hydroxyl groups; R5 and R6, which may be identical or different, represent, independently of each other, a hydrogen atom or a group chosen from the groups —(C1-C5)alkyl and the groups —(C3-C6)cycloalkyl, and also the process for preparing them and the therapeutic uses thereof.

  该发明涉及与化学式（I）对应的化合物，以其碱形式或酸盐形式存在： 其中n等于0、1、2、3或4；m等于0、1或2；o等于0或1；X代表一个基团—CH2、—CH(R′)—、—NH(R′)—或从O和S中选择的杂原子，其中R′代表一个基团—(C1-C5)烷基、—(C1-C5)烷氧基、—CH2-芳基、—C(O)R5或—COOR5；R1代表一个氧代基、—COOR5、—W—OH或—W—NR5R6；R2代表一个氢原子或从以下基团中选择的一个：(i) —(C1-C5)烷基、(ii) —(C1-C5)烷氧基、(iii) —COOR5、(iv) —NR5R6、(v) —C(O)—NR5R6、(vi) —SO2—NR3R4、(vii) 可选地被基团—(C1-C5)烷基取代的杂芳基、(viii) —W-芳基、(ix) —W-杂芳基、(x) —O—W-芳基、(xi) —O—W-杂芳基和(xii) —O—W—NR5R6；其中R3和R4，(i) 可能相同也可能不同，独立地代表一个氢原子、一个基团—(C1-C5)烷基、—(C3-C6)环烷基、芳基、杂芳基、—CH2-杂芳基、—(C1-C5)烷基-NR5R6、—W—OH或—W—NR5R6；或(ii) 与携带它们的氮原子一起形成一个杂环烷基基团，可选地取代一个或多个从以下基团中选择的基团：—(C1-C5)烷基和—CH2-芳基；W代表一个基团—(C1-C5)烷基，可选地取代一个或多个羟基；R5和R6，可能相同也可能不同，独立地代表一个氢原子或从以下基团中选择的一个：—(C1-C5)烷基和—(C3-C6)环烷基，以及其制备方法和治疗用途。