4-(4-甲基-哌啶-1-磺酰基)-苯胺 | 314285-39-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-(4-甲基-哌啶-1-磺酰基)-苯胺
• 中文别名: 4-[（4-甲基哌啶-1-基）磺酰基]苯胺
• 英文名称: 4-((4-methylpiperidin-1-yl)sulfonyl)aniline
• 英文别名: 4-(4-methylpiperidin-1-sulfonyl)phenylamine；4-methyl-1-sulfanilyl-piperidine；4-Methyl-1-sulfanilyl-piperidin；4-(4-methylpiperidine-1-sulfonyl)phenylamine；4-[(4-Methylpiperidin-1-yl)sulfonyl]aniline；4-(4-methylpiperidin-1-yl)sulfonylaniline
• CAS: 314285-39-7
• 化学式: C₁₂H₁₈N₂O₂S
• mdl: MFCD02020755
• 分子量: 254.353
• InChiKey: NTUKRLPMKLQAAE-UHFFFAOYSA-N

物化性质

• 熔点：
  110-112 °C
• 沸点：
  420.7±47.0 °C(Predicted)
• 密度：
  1.228±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  71.8
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2935009090

反应信息

• 作为反应物：
  描述：

  4-(4-甲基-哌啶-1-磺酰基)-苯胺 在 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 (S)-2-[4-(4-methylpiperidine-1-sulfonyl)phenylcarbamoyl]pyrrolidine-1-carboxylic acid benzyl ester
  参考文献：
  名称：

  WO2007/70556

  摘要：

  公开号：
• 作为产物：
  描述：

  对乙酰胺基苯磺酰氯 在 1,4-二氧六环 、 盐酸 、 碳酸氢钠 作用下， 生成 4-(4-甲基-哌啶-1-磺酰基)-苯胺
  参考文献：
  名称：

  Antitubercular Studies. V. 4-Aminobenzamides and 4-Aminobenzenesulfonamides

  摘要：

  DOI：

  10.1021/ja01143a042

文献信息

• 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。
• Structure-Based Identification of Ureas as Novel Nicotinamide Phosphoribosyltransferase (Nampt) Inhibitors
  作者：Xiaozhang Zheng、Paul Bauer、Timm Baumeister、Alexandre J. Buckmelter、Maureen Caligiuri、Karl H. Clodfelter、Bingsong Han、Yen-Ching Ho、Nikolai Kley、Jian Lin、Dominic J. Reynolds、Geeta Sharma、Chase C. Smith、Zhongguo Wang、Peter S. Dragovich、Angela Oh、Weiru Wang、Mark Zak、Janet Gunzner-Toste、Guiling Zhao、Po-wai Yuen、Kenneth W. Bair

  DOI：10.1021/jm400186h

  日期：2013.6.27

  group was the preferred substituent at one inhibitor terminus and also identified a urea moiety as the optimal linker to the remainder of the inhibitor structure. Further SAR optimization of the other inhibitor terminus ultimately yielded compound 50 as a urea-containing Nampt inhibitor which exhibited excellent biochemical and cellular potency (enzyme IC50 = 0.007 μM; A2780 IC50 = 0.032 μM). Compound

  烟酰胺磷酸核糖基转移酶（Nampt）是一种有希望的抗癌靶标。虚拟筛选确定了一种硫脲类似物化合物5为新型强效Nampt抑制剂。在5的共晶结构的指导下，SAR探索表明相应的脲化合物7表现出相似的效价，并具有改善的溶解度特征。这些研究还表明3-吡啶基是在一个抑制剂末端的优选取代基，并且还确定了脲部分是抑制剂结构其余部分的最佳连接基。另一个抑制剂末端的进一步SAR优化最终产生了化合物50作为具有尿素的Nampt抑制剂，它具有出色的生化和细胞效价（酶IC 50 = 0.007μM； A2780 IC 50 = 0.032μM）。当在A2780卵巢肿瘤异种移植模型中口服给药时，化合物50还显示出优异的体内抗肿瘤功效（在第17天观察到TGI为97％）。
• Synthesis and SAR of novel, 4-(phenylsulfamoyl)phenylacetamide mGlu4 positive allosteric modulators (PAMs) identified by functional high-throughput screening (HTS)
  作者：Darren W. Engers、Patrick R. Gentry、Richard Williams、Julie D. Bolinger、C. David Weaver、Usha N. Menon、P. Jeffrey Conn、Craig W. Lindsley、Colleen M. Niswender、Corey R. Hopkins

  DOI：10.1016/j.bmcl.2010.07.007

  日期：2010.9

  Herein we disclose the synthesis and SAR of a series of 4-(phenylsulfamoyl)phenylacetamide compounds as mGlu4 positive allosteric modulators (PAMs) that were identified via a functional HTS. An iterative parallel approach to these compounds culminated in the discovery of VU0364439 (11) which represents the most potent (19.8 nM) mGlu4 PAM reported to date.

  在此，我们公开了一系列 4-(苯基氨磺酰基)苯基乙酰胺化合物作为 mGlu 4正变构调节剂 (PAM)的合成和 SAR，这些化合物通过功能性 HTS 鉴定。对这些化合物的迭代平行方法最终发现了 VU0364439 ( 11 )，它代表了迄今为止报道的最有效 (19.8 nM) mGlu 4 PAM。
• Pharmaceutical use of substituted amides
  申请人：Andersen Sune Henrik

  公开号：US20060111366A1

  公开（公告）日：2006-05-25

  The use of substituted amides for modulating the activity of 11β-hydroxysteroid dehydrogenase type 1 (11βHSD1) and the use of these compounds as pharmaceutical compositions, are described. Also a novel class of substituted amides, their use in therapy, pharmaceutical compositions comprising the compounds, as well as their use in the manufacture of medicaments are described. The present compounds are modulators and more specifically inhibitors of the activity of 11βHSD1 and may be useful in the treatment, prevention and/or prophylaxis of a range of medical disorders where a decreased intracellular concentration of active glucocorticoid is desirable.

  本文介绍了使用取代酰胺来调节11β-羟化甾体脱氢酶1型（11βHSD1）的活性以及将这些化合物用作制药组合物的方法。还介绍了一类新型的取代酰胺，它们在治疗中的应用、包含这些化合物的制药组合物以及它们在药物制剂制造中的应用。这些化合物是11βHSD1的调节剂，更具体地说是抑制剂，可用于治疗、预防和/或预防一系列需要降低活性糖皮质激素细胞内浓度的医学疾病。
• Amide Derivatives and Pharmaceutical Use Thereof
  申请人：Andersen Henrik Sune

  公开号：US20090264414A1

  公开（公告）日：2009-10-22

  The use of substituted amides for modulating the activity of 11β-hydroxysteroid dehydrogenase type 1 (11βHSD1) and the use of these compounds as pharmaceutical compositions, are described. Also a novel class of substituted amides, their use in therapy, pharmaceutical compositions comprising the compounds, as well as their use in the manufacture of medicaments are described. The present compounds are modulators and more specifically inhibitors of the activity of 11βHSD1 and may be useful in the treatment, prevention and/or prophylaxis of a range of medical disorders where a decreased intracellular concentration of active glucocorticoid is desirable.

  本文描述了使用取代酰胺来调节11β-羟化类固醇脱氢酶1型（11βHSD1）活性以及这些化合物作为药物组分的用途。还描述了一类新型的取代酰胺，它们在治疗中的用途，包括含有这些化合物的药物组分以及它们在制造药物中的用途。这些化合物是调节剂，更具体地说是11βHSD1活性的抑制剂，可用于治疗、预防和/或预防一系列医学疾病，其中降低细胞内活性糖皮质激素的浓度是可取的。