(R/S)-4-amino-N-(1-phenylethyl)benzenesulfonamide | 79867-70-2

• 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: (R/S)-4-amino-N-(1-phenylethyl)benzenesulfonamide
• 英文别名: 4-amino-N-(1-phenylethyl)benzenesulfonamide；sulfanilic acid-(1-phenyl-ethylamide)；Sulfanilsaeure-(1-phenyl-aethylamid)
• CAS: 79867-70-2
• 化学式: C₁₄H₁₆N₂O₂S
• mdl: MFCD00544446
• 分子量: 276.359
• InChiKey: AZMQQMDSZAKUNY-UHFFFAOYSA-N

物化性质

• 熔点：
  127-129 °C(Solv: water (7732-18-5))
• 沸点：
  465.8±55.0 °C(Predicted)
• 密度：
  1.254±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  80.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  (R/S)-4-amino-N-(1-phenylethyl)benzenesulfonamide 、 4-三氟甲基苯基异氰酸酯 以 四氢呋喃 为溶剂， 反应 0.2h， 以81%的产率得到N-[(+/-)-1-phenylethyl]-{4-[3-(4-(trifluoromethyl)phenyl)urea]phenyl}sulfonamide
  参考文献：
  名称：

  Design, synthesis and in vitro antitumor evaluation of novel diaryl urea derivatives bearing sulfonamide moiety

  摘要：

  一系列具有磺酰胺基团的二芳基脲衍生物被设计和合成。通过标准的MTT法筛选和评估它们对人癌细胞系MX-1、A375、HepG2、Ketr3和HT-29的体外抗肿瘤作用，以索拉非尼作为阳性对照。一些化合物显示出相较于索拉非尼对多条细胞系显著的抑制活性。特别是2,6-二甲基-4-{6-[3-(4-氯-3-(三氟甲基)苯基)脲]萘-2-基}磺酰吗啉（10d）在A375、HepG2和Ketr3中的效能最强，其IC50值为0.65–0.97 μmol/L，效力是索拉非尼的5–20倍。化合物10d成为进一步优化的有价值的先导化合物。

  DOI：

  10.1007/s11426-013-4903-z
• 作为产物：
  描述：

  4-硝基-N-(1-苯基乙基)苯磺酰胺 在 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 4.0h， 以96.4%的产率得到(R/S)-4-amino-N-(1-phenylethyl)benzenesulfonamide
  参考文献：
  名称：

  Design, synthesis and in vitro antitumor evaluation of novel diaryl urea derivatives bearing sulfonamide moiety

  摘要：

  一系列具有磺酰胺基团的二芳基脲衍生物被设计和合成。通过标准的MTT法筛选和评估它们对人癌细胞系MX-1、A375、HepG2、Ketr3和HT-29的体外抗肿瘤作用，以索拉非尼作为阳性对照。一些化合物显示出相较于索拉非尼对多条细胞系显著的抑制活性。特别是2,6-二甲基-4-{6-[3-(4-氯-3-(三氟甲基)苯基)脲]萘-2-基}磺酰吗啉（10d）在A375、HepG2和Ketr3中的效能最强，其IC50值为0.65–0.97 μmol/L，效力是索拉非尼的5–20倍。化合物10d成为进一步优化的有价值的先导化合物。

  DOI：

  10.1007/s11426-013-4903-z

文献信息

• Acyl derivatives of p-aminosulfonamides and dapsone as new inhibitors of the arginine methyltransferase hPRMT1
  作者：Elisabeth-Maria Bissinger、Ralf Heinke、Astrid Spannhoff、Adrien Eberlin、Eric Metzger、Vincent Cura、Pierre Hassenboehler、Jean Cavarelli、Roland Schüle、Mark T. Bedford、Wolfgang Sippl、Manfred Jung

  DOI：10.1016/j.bmc.2011.02.032

  日期：2011.6

  Arginine methylation is an epigenetic modification that receives increasing interest as it plays an important role in several diseases. This is especially true for hormone-dependent cancer, seeing that histone methylation by arginine methyltransferase I (PRMT1) is involved in the activation of sexual hormone receptors. Therefore, PRMT inhibitors are potential drugs and interesting tools for cell biology. A dapsone derivative called allantodapsone previously identified by our group served as a lead structure for inhibitor synthesis. Acylated derivatives of p-aminobenzenesulfonamides and the antilepra drug dapsone were identified as new inhibitors of PRMT1 by in vitro testing. The bis-chloroacetyl amide of dapsone selectively inhibited human PRMT1 in the low micromolar region and was selective for PRMT1 as compared to the arginine methyltransferase CARM1 and the lysine methyltransferase Set7/9. It showed anticancer activity on MCF7a and LNCaP cells and blocked androgen dependent transcription specifically in a reporter gene system. Likewise, a transcriptional block was also demonstrated in LNCaP cells using quantitative RT-PCR on the mRNA of androgen dependent genes. (C) 2011 Elsevier Ltd. All rights reserved.
• Characterization of Sirtuin Inhibitors in Nematodes Expressing a Muscular Dystrophy Protein Reveals Muscle Cell and Behavioral Protection by Specific Sirtinol Analogues
  作者：Matthieu Y. Pasco、Dante Rotili、Lucia Altucci、Francesca Farina、Guy A. Rouleau、Antonello Mai、Christian Néri

  DOI：10.1021/jm9013345

  日期：2010.2.11

  In oculopharyngeal muscular dystrophy (OPMD), a disease caused by polyalanine expansion in the nuclear protein PABPN1, the genetic inhibition or sirtuins and treatment with sirtuin inhibitors protect from mutant PABPN1 toxicity in transgenic nematodes. Here, we tested the SIRT1/2 inhibitors 1-12, bearing different degrees of inhibition, for protection against mutant PABPN1 toxicity in Caenorhabditis elegans. Compounds 2, 4, and 11 were the most efficient, revealing a potential therapeutic application for muscle cell protection in OPMD.
• Discovery of Salermide-Related Sirtuin Inhibitors: Binding Mode Studies and Antiproliferative Effects in Cancer Cells Including Cancer Stem Cells
  作者：Dante Rotili、Domenico Tarantino、Angela Nebbioso、Chantal Paolini、Covadonga Huidobro、Ester Lara、Paolo Mellini、Alessia Lenoci、Riccardo Pezzi、Giorgia Botta、Maija Lahtela-Kakkonen、Antti Poso、Christian Steinkühler、Paola Gallinari、Ruggero De Maria、Mario Fraga、Manel Esteller、Lucia Altucci、Antonello Mai

  DOI：10.1021/jm3011614

  日期：2012.12.27

  Chemical changes performed on 1a (sirtinol) led to a series of SIRT1/2 inhibitors, in some cases more potent than la mainly against SIRT1. Tested in human leukemia U937 cells, the benzamide and anilide derivatives 1b, 1c, 2b, and 2c as well as the 4-(2-phenylpropyl)thioanalogue 4c showed huge apoptosis induction, while some sulfinyl and sulfonyl derivatives (5b, 5c, and 6a-c) were highly efficient in granulocytic differentiation. When assayed in human leukemia MOLT4 as well as in human breast MDA-MB-231 and colon RKO cancer cell lines, the anilide 2b (salermide) and the phenylpropylthio analogue 4b emerged as the most potent antiproliferative agents. Tested on colorectal carcinoma and glioblastoma multiforme cancer stem cells (CSCs) from patients, 2b was particularly potent against colorectal carcinoma CSCs, while 4b, 6a, and the SIRT2-selective inhibitor AGK-2 showed the highest effect against glioblastoma multiforme CSCs. Such compounds will be further explored for their broad-spectrum anticancer properties.
• Design, synthesis and in vitro antitumor evaluation of novel diaryl urea derivatives bearing sulfonamide moiety
  作者：Can Luo、Ke Tang、Yan Li、DaLi Yin、XiaoGuang Chen、HaiHong Huang

  DOI：10.1007/s11426-013-4903-z

  日期：2013.11

  A novel series of diaryl urea derivatives bearing sulfonamide moiety have been designed and synthesized. Their in vitro antitumor effect against human cancer cell lines MX-1, A375, HepG2, Ketr3 and HT-29 was screened and evaluated by the standard MTT assay with sorafenib as the positive control. Some of the compounds showed significant inhibitory activity against multiple cell lines compared to sorafenib. In particular, 2,6-dimethyl-4-6-[3-(4-chloro-3-(trifluoromethyl)phenyl)urea]naphthalen-2-yl}sulfonyl morpholine (10d) was found to be the most potent against A375, HepG2 and Ketr3 with IC50 values of 0.65–0.97 μmol/L, which were 5–20-fold more potent than sorafenib. Compound 10d emerged as a valuable lead for further optimization.

  一系列具有磺酰胺基团的二芳基脲衍生物被设计和合成。通过标准的MTT法筛选和评估它们对人癌细胞系MX-1、A375、HepG2、Ketr3和HT-29的体外抗肿瘤作用，以索拉非尼作为阳性对照。一些化合物显示出相较于索拉非尼对多条细胞系显著的抑制活性。特别是2,6-二甲基-4-6-[3-(4-氯-3-(三氟甲基)苯基)脲]萘-2-基}磺酰吗啉（10d）在A375、HepG2和Ketr3中的效能最强，其IC50值为0.65–0.97 μmol/L，效力是索拉非尼的5–20倍。化合物10d成为进一步优化的有价值的先导化合物。