N-(3-甲氧基苯基)苯磺酰胺 | 22865-27-6

• 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: N-(3-甲氧基苯基)苯磺酰胺
• 英文名称: N-(3-methoxyphenyl)benzenesulfonamide
• CAS: 22865-27-6
• 化学式: C₁₃H₁₃NO₃S
• mdl: MFCD01231444
• 分子量: 263.317
• InChiKey: PIGMPCQZRHHQIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.076
• 拓扑面积：
  63.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(3-甲氧基苯基)苯磺酰胺 在 三氯化铝 、 三氟化硼乙醚 、 碳酸氢钠 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.75h， 生成 (6-methoxy-1H-indol-3-yl)(3,4,5-trimethoxyphenyl)methanone
  参考文献：
  名称：

  Synthesis and biological evaluation of (3,4,5-trimethoxyphenyl)indol-3-ylmethane derivatives as potential antivascular agents

  摘要：

  Combretastatin A-4 (CSA-4), a stilbene derivative, is a potent vascular disrupting agent (VDA) with the structural requirement of a cis-configuration to maintain a molecular geometry and a correct orientation of both phenyl groups. A series of indolic analogues of CSA-4 was synthesized by means of an efficient strategy. Six compounds (20b, 25b-27b, 32b, and 35b) were identified as potent inhibitors of tubulin polymerization and also displayed cytotoxic activities on B16 melanoma cells at a nanomolar level. Both activities were well correlated with the ability to induce morphological changes of EA-hy 926 endothelial cells. In conclusion, the cis-stilbene skeleton of CSA-4 could conveniently be replaced by the 3-aroylindolic moiety, thus avoiding any isomerization leading to inactive trans compounds. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.02.037
• 作为产物：
  描述：

  苯磺酰基叠氮化物 在 bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] 、 lithium acetate 、 palladium diacetate 、 双三氟甲烷磺酰亚胺银盐 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 36.0h， 生成 N-(3-甲氧基苯基)苯磺酰胺
  参考文献：
  名称：

  直接C ？苯甲酸的H酰胺化通过串联脱羧引入间氨基和对氨基

  摘要：

  开发了具有磺酰叠氮化物的苯甲酸的Ir催化轻度CH酰胺化反应，可实现高效且具有官能团相容性的反应。随后，将氨基酰胺化的邻氨基苯甲酸产物进行原羧化反应，可得到间位或对位取代的（N-磺酰基）苯胺衍生物，而其他CH官能化方法则无法获得后者。脱羧步骤与酰胺化条件兼容，可实现方便的一锅两步工艺。

  DOI：

  10.1002/chem.201500331

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。
• Sulfonamidation of Aryl and Heteroaryl Halides through Photosensitized Nickel Catalysis
  作者：Taehoon Kim、Stefan J. McCarver、Chulbom Lee、David W. C. MacMillan

  DOI：10.1002/anie.201800699

  日期：2018.3.19

  highly efficient method for nickel‐catalyzed C−N bond formation between sulfonamides and aryl electrophiles. This technology provides generic access to a broad range of N‐aryl and N‐heteroaryl sulfonamide motifs, which are widely represented in drug discovery. Initial mechanistic studies suggest an energy‐transfer mechanism wherein C−N bond reductive elimination occurs from a triplet excited NiII complex

  本文中，我们报告了一种在磺酰胺和芳基亲电试剂之间形成镍催化的C-N键的高效方法。这项技术为获得广泛的N-芳基和N-杂芳基磺酰胺基序提供了通用途径，这在药物研发中得到了广泛的体现。最初的力学研究表明，一种能量转移机理是C-N键的还原消除是由三重激发的Ni II络合物引起的。还证明了在药理学相关结构合成中的后期磺酰胺化作用。
• Pro-Neurogenic Compounds
  申请人：Board of Regents of The University of Texas System

  公开号：US20140057900A1

  公开（公告）日：2014-02-27

  Compounds and methods for stimulating neurogenesis (e.g., post-natal neurogenesis, including post-natal hippocampal and hypothalamic neurogenesis) and/or protecting neuronal cell from cell death are disclosed herein. In vivo activity tests suggest that these compounds may have therapeutic benefits in neuropsychiatric and/or neurodegenerative diseases such as schizophrenia, major depression, bipolar disorder, normal aging, epilepsy, traumatic brain injury, post-traumatic stress disorder, Parkinson's disease, Alzheimer's disease, Down syndrome, spinocerebellar ataxia, amyotrophic lateral sclerosis, Huntington's disease, stroke, radiation therapy, chronic stress, abuse of a neuro-active drug, retinal degeneration, spinal cord injury, peripheral nerve injury, physiological weight loss associated with various conditions, as well as cognitive decline associated with normal aging, chemotherapy, and the like.

  本发明公开了刺激神经发生（例如，产后神经发生，包括产后海马和下丘脑神经发生）和/或保护神经细胞免于细胞死亡的化合物和方法。体内活性测试表明，这些化合物可能在精神神经疾病和/或神经退行性疾病中具有治疗益处，例如精神分裂症、重度抑郁症、双相情感障碍、正常衰老、癫痫、创伤性脑损伤、创伤后应激障碍、帕金森病、阿尔茨海默病、唐氏综合症、脊髓小脑共济失调、肌萎缩侧索硬化症、亨廷顿病、中风、放射治疗、慢性压力、滥用神经活性药物、视网膜退化、脊髓损伤、周围神经损伤、与各种情况相关的生理体重减轻，以及与正常衰老、化疗等相关的认知衰退。
• [EN] PIPERIDINE-BENZENESULFONAMIDE DERIVATIVES<br/>[FR] DERIVES DE PIPERIDINE-BENZENESULFONAMIDE
  申请人：HOFFMANN LA ROCHE

  公开号：WO2004072034A1

  公开（公告）日：2004-08-26

  The present invention relates to compounds of the general formula (I) wherein R1 is lower alkyl, -(CH2)n-aryl, unsubstituted or substituted by one or two substituents, selected from the group consisting of lower alkyl, lower alkoxy, -OCF3, halogen, -NR’R” or trifluoromethyl, or heteroaryl; R2 is lower alkyl, -(CH2)n-aryl, unsubstituted or substituted by one or two substituents, selected from the group consisting of lower alkyl, lower alkoxy, halogen, trifluoromethyl, nitro, cyano, -NR’R”, hydroxy, or by a heteroaryl group, or is heteroaryl, unsubstituted or substituted by one or two substituents, selected from the group consisting of lower alkyl or halogen; R3 is heteroaryl or is aryl, unsubstituted or substituted by halogen or lower alkyl; R4 is hydrogen or hydroxy; A is -S(O)2-or-C(O)-; X,Y are independently from each other -CH2- or -O-, with the proviso that X and Y are not simultaneously -O; R’R” are independently from each other hydrogen, lower alkyl or -C(O)-lower alkyl; n is 0, 1 or 2; and to pharmaceutically acceptable acid addition salts thereof. The compounds may be used for the treatment of psychoses, pain, disfunction in memory and learning, schizophrenia, dementia and other diseases in which cognitive processes are impaired, such as attention deficit disorders or Alzheimer’s disease.

  本发明涉及一般式（I）的化合物，其中R1为较低的烷基，-(CH2)n-芳基，未取代或被选自较低烷基、较低烷氧基、-OCF3、卤素、-NR’R”或三氟甲基的一种或两种取代基所取代，或杂芳基；R2为较低的烷基，-(CH2)n-芳基，未取代或被选自较低烷基、较低烷氧基、卤素、三氟甲基、硝基、氰基、-NR’R”、羟基，或由杂芳基所取代的一种或两种取代基，或为杂芳基，未取代或被选自较低烷基或卤素的一种或两种取代基；R3为杂芳基或为芳基，未取代或被卤素或较低烷基所取代；R4为氢或羟基；A为-S(O)2-或-C(O)-；X，Y分别为-CH2-或-O-，但X和Y不能同时为-O；R’R”分别为氢、较低烷基或-C(O)-较低烷基；n为0、1或2；以及其药学上可接受的酸盐。这些化合物可用于治疗精神病、疼痛、记忆和学习功能障碍、精神分裂症、痴呆症和其他认知过程受损的疾病，如注意力缺陷障碍或阿尔茨海默病。
• Copper-catalyzed N-arylation of sulfonamides with aryl bromides and iodides using microwave heating
  作者：Huan He、Yong-Jin Wu

  DOI：10.1016/s0040-4039(03)00569-0

  日期：2003.4

  The copper-catalyzed N-arylation of sulfonamides with a variety of aryl bromides and iodides using microwave heating is described.

  描述了使用微波加热的铜催化的磺酰胺与各种芳基溴化物和碘化物的N-芳基化。