(E)-N-(4-isopropyl-benzylidene)-4-methylbenzenesulfonamide | 951762-66-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (E)-N-(4-isopropyl-benzylidene)-4-methylbenzenesulfonamide
• 英文别名: N-(4-Isopropylbenzylidene)-4-methylbenzenesulfonamide；(NE)-4-methyl-N-[(4-propan-2-ylphenyl)methylidene]benzenesulfonamide
• CAS: 951762-66-6
• 化学式: C₁₇H₁₉NO₂S
• 分子量: 301.409
• InChiKey: QDNWKNMMUMIPAK-LDADJPATSA-N

物化性质

• 熔点：
  110-112 °C
• 沸点：
  436.3±48.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  54.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(3-chlorobenzyl)-2,3-butadienoic acid 、 (E)-N-(4-isopropyl-benzylidene)-4-methylbenzenesulfonamide 在 2-氯-1-甲基吡啶碘化物 、 三乙胺 、 三丁基膦 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 124.0h， 生成 2-(3-chlorophenyl)-6-(4-isopropylphenyl)-1-(4-toluenesulfonyl)-1,2,5,6-tetrahydropyridine-3-carboxylic acid
  参考文献：
  名称：

  Small-Molecule Inhibitors of Protein Geranylgeranyltransferase Type I

  摘要：

  Small molecules that inhibit the geranylgeranylation of K-Ras4B and RhoA by protein geranylgeranyltransferase type I (GGTase-I) were identified from chemical genetic screens of heterocycles synthesized through phosphine catalysis of allenes. To further improve the efficacy of the GGTase-I inhibitors (GGTIs), 4288 related compounds bearing core dihydropyrrole/pyrrolidine and tetrahydropyridine/piperidine scaffolds were synthesized on SynPhase lanterns in a split-pool manner through phosphine-catalyzed [3 + 2] and [4 + 2] annulations of resin-bound allenoates. Testing of the 4288 analogues resulted in several GGTIs exhibiting submicromolar IC50 values. Because proteins such as Ras and Rho GTPases are implicated in oncogenesis and metastasis, these GGTIs might ultimately lead to the development of novel antitumor therapeutics.

  DOI：

  10.1021/ja070274n
• 作为产物：
  描述：

  对甲苯磺酰胺 、 4-异丙基苯甲醛 以 乙醇 为溶剂， 生成 (E)-N-(4-isopropyl-benzylidene)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  潜在的抗菌剂和抗病毒剂取代苯基氮杂环丁烷-2-酮磺酰基衍生物的合成及生物学评价

  摘要：

  在本研究中，我们打算合成一系列新颖的取代苯基氮杂环丁烷-2-酮磺酰基衍生物。筛选了整套衍生物5（at）的体外抗菌和抗真菌活性，并进一步筛选了其中的11种化合物的抗病毒活性，以预测其对抗病原体病毒的功效。有趣的是，与氨苄青霉素（标准品）相比，化合物5d，5e，5f，5h，5i和5j表现出相似或更好的抗菌活性。此外，化合物5h，5i，5j和5q与标准药物克霉唑相比，对真菌菌株具有良好的抑制活性，而其他衍生物的活性较弱或减弱。抗菌研究表明，具有吸电子基团的化合物显示出最高的活性。有趣的是，这些测试的化合物在HEL细胞，Vero细胞和MDCK细胞培养物中对牛痘病毒，人冠状病毒（229E），呼肠孤病毒1，辛德比斯病毒，柯萨奇病毒B4，黄热病病毒和乙型流感病毒显示弱的抗病毒活性。本研究的发现可能会开辟新途径，以针对人类致病的致命微生物和病毒。

  DOI：

  10.1016/j.bioorg.2020.104320

文献信息

• Trimethylsilyl cyanide addition to aldimines and its application in the synthesis of (S)-phenylglycine methyl ester
  作者：B.A. Bhanu Prasad、Alakesh Bisai、Vinod K. Singh

  DOI：10.1016/j.tetlet.2004.11.015

  日期：2004.12

  reaction) in the presence of LiClO4 or BF3·Et2O in acetonitrile has been studied. The reaction provided the addition products in very high yields. The method has been successfully utilized for the synthesis of (S)-phenylglycine methyl ester.

  已经研究了在乙腈中存在LiClO 4或BF 3 ·Et 2 O的情况下，向各种芳基醛亚胺中添加TMSCN（斯特雷克反应）。该反应以非常高的产率提供了加成产物。该方法已成功地用于合成（S）-苯基甘氨酸甲酯。
• Triarylmethyl chlorides as novel, efficient, and mild organic catalysts for the synthesis of <i>N</i>-sulfonyl imines under neutral conditions
  作者：Ali Khalafi-Nezhad、Abolfath Parhami、Abdolkarim Zare、Amir Nasrolahi Shirazi、Ahmad Reza Moosavi Zare、Alireza Hassaninejad

  DOI：10.1139/v08-039

  日期：2008.5.1

  A highly efficient procedure for the preparation of N-sulfonyl imines via condensation of sulfonamides with aldehydes as well as ketones in the presence of triarylmethyl chlorides as metal-free organo-catalysts at 40 °C is described. The advantages of this class of catalysts over the reported ones are their efficiency and possibility of running reactions in neutral media that makes them suitable for

  描述了一种通过磺酰胺与醛以及酮在三芳基甲基氯作为无金属有机催化剂存在下在 40°C 下缩合制备 N-磺酰基亚胺的高效方法。与报道的催化剂相比，这类催化剂的优势在于它们的效率和在中性介质中进行反应的可能性，这使得它们适用于对酸敏感的底物。关键词：三芳基甲基氯、N-磺酰基亚胺、磺酰胺、醛、酮。
• A highly diastereoselective synthesis of 3-carbethoxy-2,5-disubstituted-3-pyrrolines by phosphine catalysis
  作者：Xue-Feng Zhu、Christopher E. Henry、Ohyun Kwon

  DOI：10.1016/j.tet.2005.03.104

  日期：2005.6

  Tributylphosphine was used as catalyst to facilitate a [3+2] cycloaddition between gamma-substituted allenoates and N-sulfonylimines. The resulting adducts, 3-carbethoxy-2,5-disubstituted-3-pyrrolines were formed in excellent yields with high diastereoselectivity. The reaction went to completion in several hours at room temperature, and the starting materials were easily prepared with one step from commercially available compounds via known procedures. (c) 2005 Elsevier Ltd. All rights reserved.
• Green, Catalyst-Free Protocol for the Efficient Synthesis of N-Sulfonyl Aldimines and Ketimines in Ionic Liquid [Bmim]Br
  作者：Abdolkarim Zare、Ahmad Reza Moosavi-Zare、Alireza Hasaninejad、Abolfath Parhami、Ali Khalafi-Nezhad、Mohammad Hassan Beyzavi

  DOI：10.1080/00397910902731000

  日期：2009.7.29

  Sulfonamides are efficiently condensed with aldehydes as well as ketones in the absence of catalyst in 1-butyl-3-methylimidazolium bromide ([bmim]Br) under microwave irradiation to afford N-sulfonyl aldimines and ketimines in good to excellent yields in short reaction times.
• INHIBITORS OF PROTEIN PRENYLTRANSFERASES
  申请人：Kwon Ohyun

  公开号：US20110178138A1

  公开（公告）日：2011-07-21

  The present invention is directed to novel compounds. These compounds can be useful in inhibiting the activity of protein prenyltransferases including GGTase I and/or RabGGTase. The compounds can also be used as anti-cancer therapeutics including as part of methods for treating cancer, in assays, and in kits.