methyl 2-(N-(p-tolyl)sulfamoyl)acetate | 1136056-24-0

• 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: methyl 2-(N-(p-tolyl)sulfamoyl)acetate
• 英文别名: methyl 2-[(4-methylphenyl)sulfamoyl]acetate
• CAS: 1136056-24-0
• 化学式: C₁₀H₁₃NO₄S
• 分子量: 243.284
• InChiKey: DCOYCOLKZJWMBY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  80.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2-(N-(p-tolyl)sulfamoyl)acetate 在 吡啶 、 sodium hydride 、 一水合肼 、 三氯氧磷 作用下， 以 甲醇 、 乙醚 、 二甲基亚砜 为溶剂， 生成 2-(p-methylphenylaminosulfonylmethyl)-5-(4-(p-methylphenyl)-1H-pyrrol-3-ylsulfonylmethyl)-1,3,4-oxadiazole
  参考文献：
  名称：

  吡咯基/吡唑基芳基氨基磺酰基甲基1,3,4-恶二唑，1,3,4-噻二唑和1,2,4-三唑的合成及抑菌活性。

  摘要：

  制备了新型的吡咯基/吡唑基芳基氨基磺酰基甲基1,3,4-恶二唑，1,3,4-噻二唑和1,2,4-三唑并测试了其抗菌活性。在测试的化合物中，5c表现出高抗菌活性。

  DOI：

  10.1248/cpb.59.1509
• 作为产物：
  描述：

  甲醇 、 2-(N-(对甲苯基)氨磺酰基)乙酸 在 硫酸 作用下， 生成 methyl 2-(N-(p-tolyl)sulfamoyl)acetate
  参考文献：
  名称：

  双（芳基磺酰基甲基/芳基氨基磺酰基甲基偶氮基）吡啶的合成，表征和抗氧化活性

  摘要：

  采用绿色方法超声法，由合成中间体甲基芳基磺酰基乙酸酰肼和甲基芳基氨基磺酰基乙酸酰肼合成了新型的双（芳基磺酰基甲基偶氮基）吡啶和双（芳基氨基磺酰基甲基-偶氮基）吡啶。所有合成的化合物均具有较高的收率和较短的反应时间。光谱参数，例如IR，1 H NMR，13 C NMR，质量和微量分析用于确定所有合成化合物的结构，并测定其抗氧化活性。的双（arylaminosulfonylmethylazolyl）吡啶显示出更高的自由基清除活性比二（芳基磺酰基甲基偶氮基）吡啶。此外，未取代的和甲基取代的化合物表现出更大的活性。在所有测试化合物中，8b和11b被确定为潜在的抗氧化剂。

  DOI：

  10.1002/jhet.4123

文献信息

• Straightforward Route to γ-Sultams via Novel Tandem SN/Michael Addition
  作者：Olga Bakulina、Anastasiia Klochkova、Andrey Bubyrev、Dmitry Dar’in、Mikhail Krasavin、Viktor Sokolov

  DOI：10.1055/a-1343-9451

  日期：2021.5

  A novel tandem approach to trisubstituted γ-sultams has been developed involving N-alkylation of methanesulfonanilides with EWG-substituted allyl bromides followed by intramolecular Michael addition. A series of various isothiazolidine 1,1-dioxides have been prepared under mild transition-metal-free conditions in high yields and trans-diastereoselectivity (confirmed by X-ray crystallography). The dependence

  已经开发出一种新颖的串联三取代的γ-sultams方法，包括用EWG取代的烯丙基溴对甲磺酰苯胺进行N-烷基化，然后进行分子内迈克尔加成。已在温和的无过渡金属条件下以高收率和反式非对映选择性（由X射线晶体学证实）制备了一系列各种异噻唑烷1,1-二氧化物。已经研究了反应性对基材的电子性能的依赖性。
• Synthesis and Evaluation of Antiepileptic Activity of Newly Designed Coumarin-Sulfonamide Hybrids
  作者：Arti Gupta、Sandeep Kumar、Vijay Kumar Singh、B.P. Mallikarjun、Neerupma Dhiman、Archana Sharma

  DOI：10.14233/ajchem.2021.23527

  日期：——

  The combination of different heterocyclic rings to form a multifunctional compound is a new approach to get the potent and selective compounds, which can act as antiepileptic drugs. In this study we designed and synthesized the hybrid of the coumarin ring with sulfonamide moiety. Coumarin sulfonamide hybrids (CS1-CS7) were synthesized by Knoevenagel condensation of methyl anilinosulfonyl acetate with substituted salicyaldehyde in the presence of catalytic base. The synthesized hybrid compounds were characterized by means of mass, 1H & 13C NMR and FTIR spectroscopy, moreover antiepileptic activity was screened through seizure model of epilepsy using pentylenetetrazole and maximal electroshock. According to results, compound CS-2 remained to be highest potent and presented significant protection at 60 mg/kg in both the seizure models. Furthermore, compound CS-2 was also evaluated for biochemical and a histopathological study in which no significant results were obtained. In addition to former activities, compound CS-2 was also examined for liver toxicity.

  不同的杂环环状结构组合形成多功能化合物是一种新的方法，可以获得有效且选择性的化合物，可作为抗癫痫药物。在这项研究中，我们设计并合成了香豆素环与磺酰胺基团的杂交物。通过催化碱存在下，将甲基苯胺磺酰酸乙酯与取代水杨醛进行Knoevenagel缩合反应，合成了香豆素磺酰胺杂化物（CS1-CS7）。通过质谱、1H和13C NMR以及FTIR光谱对合成的杂化物进行了表征，此外，通过戊四氮和最大电击发作的癫痫模型筛选了抗癫痫活性。根据结果，化合物CS-2表现出最高的有效性，并在两种癫痫模型中以60 mg/kg呈现出显著的保护作用。此外，还对化合物CS-2进行了生化和组织病理学研究，未获得显著结果。除了前面的活性外，还对化合物CS-2进行了肝毒性评估。
• Synthesis of a New Class of Sulfonamido Bis Heterocycles-Pyrrolyl/Pyrazolyl-1,3,4-oxadiazoles, 1,3,4-Thiadiazoles, and 1,2,4-Triazoles
  作者：Akkarapalli Muralikrishna、Guda Mallikarjuna Reddy、Gopala Lavanya、Venkatapuram Padmavathi、Adivireddy Padmaja

  DOI：10.1002/jhet.1679

  日期：2014.1

  A new class of sulfonamido bis heterocycles—pyrrolyl/pyrazolyl‐oxadiazoles, thiadiazoles, and triazoles—were prepared from arylaminosulfonylacetic acid hydrazide and E‐aroylethenesulfonylacetic acid adopting simple and versatile synthetic methodologies.

  采用简单而通用的合成方法，由芳基氨基磺酰乙酸酰肼和E-芳酰基乙磺酰磺酸制备了新型的磺酰胺基双杂环-吡咯基/吡唑基-恶二唑，噻二唑和三唑。
• Synthesis and bioassay of aminosulfonyl-1,3,4-oxadiazoles and their interconversion to 1,3,4-thiadiazoles
  作者：V. Padmavathi、S. Nagi Reddy、G. Dinneswara Reddy、A. Padmaja

  DOI：10.1016/j.ejmech.2010.06.022

  日期：2010.9

  A new class of oxadiazoles is prepared by treating aminosulfonylacetic acids with different carboxylic acid hydrazides. Interconversion of oxadiazoles to thiadiazoles is carried out with thiourea. The compounds are screened for antimicrobial and antioxidant activities. (C) 2010 Elsevier Masson SAS. All rights reserved.
• Synthesis of sultams by cycloalkylation of (alkoxycarbonylmethane)sulfonanilides
  作者：V. A. Rassadin、A. A. Tomashevskii、V. V. Sokolov、A. A. Potekhin

  DOI：10.1007/s10593-008-0066-9

  日期：2008.4

  (Methoxycarbonylmethane)sulfonanilides are alkylated by alpha, omega-dihaloalkanes in K(2)CO(3)-DMF with the formation of sultams. A high sensitivity has been detected for the reaction rate on the electronic effect of substituents in the aromatic nucleus, although substituents in the ortho position do not obstruct the reaction and in the case of 2,6-disubstituted derivatives the reaction rate and sultam yield were maximal. Tertiary sulfonamides form derivatives of 1-sulfamoylcyclopropanecarboxylic acid under these conditions.