2-(phenylsulfonamido)-1-ethylbenzene | 84416-67-1

• 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-(phenylsulfonamido)-1-ethylbenzene
• 英文别名: benzenesulfonic acid-(2-ethyl-anilide)；Benzolsulfonsaeure-(2-aethyl-anilid)；2-Benzolsulfamino-1-aethyl-benzol；N-(2-ethylphenyl)benzenesulfonamide
• CAS: 84416-67-1
• 化学式: C₁₄H₁₅NO₂S
• mdl: MFCD00586676
• 分子量: 261.345
• InChiKey: PNYMUYWIOOASLZ-UHFFFAOYSA-N

物化性质

• 熔点：
  110-111 °C
• 沸点：
  402.4±38.0 °C(Predicted)
• 密度：
  1.236±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-methoxy-6-(trimethylsilyl)phenyltrifluoromethanesulfonate 、 2-(phenylsulfonamido)-1-ethylbenzene 在 cesium fluoride 作用下， 以 乙腈 为溶剂， 以82 %的产率得到N-(2-ethylphenyl)-N-(3-methoxyphenyl)benzenesulfonamide
  参考文献：
  名称：

  N,N‐Diarysulfonamide reduces proinflammatory cytokine interleukin‐6 levels in cells through nuclear factor‐κB regulation

  摘要：

  The synthesized sulfonamides were evaluated for cytotoxicity followed by the cytokine/inflammatory marker’s inhibition capability and its mechanism of action in RAW‐264.7 cells. Elevated interleukin‐6 (IL‐6) levels have been reported in inflammatory conditions and inflammation‐associated disorders. Hence, reducing the IL‐6 levels in inflammatory conditions can serve as an attractive therapeutic target in dealing the inflammation. Among 42 compounds, seven compounds showed significant inhibition of IL‐6 levels in lipopolysaccharide (LPS) challenged RAW‐264.7 cells at 12.5 µM concentration. Further, investigation revealed that the IC50 value of these compounds for reducing IL‐6 levels was found to be in the range of 9.7 to 2.6 µM. The promising compounds 5y (IC50 of 2.6 µM) and 5n (IC50 of 4.1 µM) along with other derivatives fulfil drug‐likeness parameters laid down by Lipinski’s rule of five. Further, analysis using RTqPCR and Western‐blot analysis revealed that treatment with 5n significantly reduced the expression of pro‐inflammatory, inflammatory and macrophage marker’s expression (IL‐1β, CCL2, COX2 and CD68) compared to LPS control. The mechanistic evaluation showed that RL‐442 exhibited anti‐inflammatory properties by modulating the nuclear factor‐κB (NF‐κB) activation. The identified compound can be a promising candidate for further discovery efforts to generate a preclinical candidate effective in inflammation.

  DOI：

  10.1002/cmdc.202300598
• 作为产物：
  描述：

  2,3-diiodo-1-(phenylsulfonyl)indole 在 palladium on activated charcoal 氢气 、 叔丁基锂 、 氯化铵 作用下， 以 四氢呋喃 、 乙醇 为溶剂， -100.0 ℃ 、303.98 kPa 条件下， 反应 19.58h， 生成 2-(phenylsulfonamido)-1-ethylbenzene
  参考文献：
  名称：

  Generation and ring-opening of 2,3-dilithio-1-(phenylsulfonyl)indole

  摘要：

  DOI：

  10.1021/jo00152a041

文献信息

• Characteristic Hydrogen Bonding Observed in the Crystals of Aromatic Sulfonamides: 1D Chain Assembly of Molecules and Chiral Discrimination on Crystallization
  作者：Shoko Kikkawa、Hyuma Masu、Kosuke Katagiri、Misaki Okayasu、Kentaro Yamaguchi、Hiroshi Danjo、Masatoshi Kawahata、Masahide Tominaga、Yoshihisa Sei、Hidemasa Hikawa、Isao Azumaya

  DOI：10.1021/acs.cgd.9b00159

  日期：2019.5.1

  achiral, except for kryptoracemates. In contrast, a high proportion of compounds with Helical or Straight patterns in the crystals showed chiral crystallization. Our classification is useful for discussion regarding the chirality of molecular assemblies, on the basis of the conformational chirality of the molecules in the crystal.

  N-苯基苯磺酰胺优先存在于（+）-或（-顺式构象，将芳香环的两端在相同方向上加捻。我们已经系统地分析了在苯环上带有甲基，乙基和/或甲氧基的仲芳族磺酰胺的晶体结构。在85个晶体中，有81个观察到了磺酰胺质子和磺酰氧之间的分子间氢键。分子间氢键键合模式可分为四种类型，即二聚体，锯齿形，螺旋形和直链型，并保留磺酰胺部分的向斜构象。我们研究了氢键模式与显示手性结晶的化合物比例之间的关系。根据我们对芳香族磺酰胺分子间氢键的分类，具有二聚体和锯齿形图案的晶体，它们都具有对映体向斜构象异构体，除了k酸酯外消旋体，它们本质上是非手性的。相反，晶体中大部分具有螺旋或直形图案的化合物显示出手性结晶。基于晶体中分子的构象手性，我们的分类对于讨论分子组装的手性有用。
• [EN] ALKYLUREA DERIVATIVES ACTIVE AGAINST CANCER CELLS<br/>[FR] DÉRIVÉS D'ALKYLURÉE ACTIFS CONTRE LES CELLULES CANCÉREUSES
  申请人：UNIV LAVAL

  公开号：WO2012142698A1

  公开（公告）日：2012-10-26

  Compounds of formula (I) : wherein A, m, n, R1, X, Y, R2, R3, R4, R5 and R6, as defined herein are provided as useful for the treatment of cancer or for the manufacture of anti-cancer agents.

  化合物的化学式（I）：其中A、m、n、R1、X、Y、R2、R3、R4、R5和R6的定义如下，在此处被提供作为治疗癌症或制造抗癌药物的有用化合物。
• FIVE-MEMBERED HETEROCYCLES USEFUL AS SERINE PROTEASE INHIBITORS
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：US20150259297A1

  公开（公告）日：2015-09-17

  The present invention provides a method for treating a thrombotic or an inflammatory disorder administering to a patient in need thereof a therapeutically effective amount of at least one compound of Formula (I) or Formula (V): or a stereoisomer or pharmaceutically acceptable salt or solvate form thereof, wherein the variables A, L, Z, R 3 , R 4 , R 6 , R 11 , X 1 , X 2 , and X 3 are as defined herein. The compounds of Formula (I) are useful as selective inhibitors of serine protease enzymes of the coagulation cascade and/or contact activation system; for example thrombin, factor Xa, factor XIa, factor IXa, factor VIIa and/or plasma kallikrein. In particular, it relates to compounds that are selective factor XIa inhibitors. This invention also provides compounds within the scope of Formula I and relates to pharmaceutical compositions comprising these compounds.

  本发明提供了一种治疗血栓性或炎症性疾病的方法，包括向需要治疗的患者施用至少一种化合物的治疗有效量，该化合物为公式（I）或公式（V）中的至少一种，或其立体异构体或药学上可接受的盐或溶剂形式，其中变量A、L、Z、R3、R4、R6、R11、X1、X2和X3的定义如本文所述。公式（I）中的化合物可用作凝血级联和/或接触激活系统的丝氨酸蛋白酶酶的选择性抑制剂，例如凝血酶、因子Xa、因子XIa、因子IXa、因子VIIa和/或血浆激肽原。特别是，涉及到选择性因子XIa抑制剂的化合物。本发明还提供了公式I范围内的化合物，并涉及包含这些化合物的药物组合物。
• GRIBBLE, G. W.;SAULNIER, M. G., J. ORG. CHEM., 1983, 48, N 4, 607-609
  作者：GRIBBLE, G. W.、SAULNIER, M. G.

  DOI：——

  日期：——
• US8716492B2
  申请人：——

  公开号：US8716492B2

  公开（公告）日：2014-05-06