1-(3,5-dimethylphenylthio)pyrrolidine-2,5-dione | 473258-21-8

• 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: 1-(3,5-dimethylphenylthio)pyrrolidine-2,5-dione
• 英文别名: N-[(3,5-dimethylphenyl)thio]succinimide；N-(3,5-dimethylphenylthio)succinimide；1-(3,5-dimethylphenyl)sulfanylpyrrolidine-2,5-dione
• CAS: 473258-21-8
• 化学式: C₁₂H₁₃NO₂S
• 分子量: 235.307
• InChiKey: FBGVDFDYCUOIGO-UHFFFAOYSA-N

物化性质

• 熔点：
  131-134 °C
• 沸点：
  377.7±52.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  62.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(3,5-dimethylphenylthio)pyrrolidine-2,5-dione 在 三氟化硼乙醚 、 一水合肼 、 间氯过氧苯甲酸 作用下， 以 乙醇 、 二氯甲烷 、 氯仿 为溶剂， 反应 7.0h， 生成 5-chloro-3-(3,5-dimethylphenyl)sulfonyl-1H-indole-2-carbohydrazide
  参考文献：
  名称：

  Novel Indolyl Aryl Sulfones Active against HIV-1 Carrying NNRTI Resistance Mutations:  Synthesis and SAR Studies

  摘要：

  The potent anti-HIV-1 activities of L-737,126 (2) and PAS sulfones prompted us to design and test against HIV-1 in acutely infected MT-4 cells a number of novel 1- and 3-benzenesulfonylindoles. Indoles belonging to the 1-benzenesulfonyl series were found poorly or totally inactive. On the contrary, some of the 3-benzenesulfonyl derivatives turned out to be as potent as 2, being endowed with potencies in the low nanomolar concentration range. In particular, (2-methylphenyl)sulfonyl (72) and (3-methylphenyl)sulfonyl (73) derivatives showed EC50 values of 1 nM. Introduction of two methyl groups at positions 3 and 5 of the phenyl ring of 2 furnished derivatives (80 and 83) which showed very potent and selective anti-HIV-1 activity not only against the wt strain, but also against mutants carrying NNRTI-resistant mutations at positions 103 and 181 of the reverse transcriptase gene.

  DOI：

  10.1021/jm0211063
• 作为产物：
  描述：

  N-氯代丁二酰亚胺 、 3,5-二甲基苯硫酚 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 1-(3,5-dimethylphenylthio)pyrrolidine-2,5-dione
  参考文献：
  名称：

  布朗斯台德酸促进炔烃的磺基酰氧基化：获得 4-磺基异香豆素

  摘要：

  本文介绍的是布朗斯台德酸 (MsOH) 介导的邻炔基苯甲酸酯的亲电子硫酰酰氧基化反应，该反应通过由工作台稳定的N-硫代芳基/烷基-琥珀酰亚胺原位形成的锍阳离子进行炔烃活化，然后进行分子内区域选择性环化。该转化提供了以 77-98% 的产率获得结构多样的 4-亚磺基异香豆素，并具有广泛的官能团兼容性。邻苯二甲酰亚胺保护基团的反应可扩展性和可重复使用性使该协议在综合上可行。

  DOI：

  10.1002/adsc.202200761

文献信息

• Simple, Short Peptide Derivatives of a Sulfonylindolecarboxamide (L-737,126) Active in Vitro against HIV-1 Wild Type and Variants Carrying Non-Nucleoside Reverse Transcriptase Inhibitor Resistance Mutations
  作者：Romano Silvestri、Marino Artico、Gabriella De Martino、Giuseppe La Regina、Roberta Loddo、Massimiliano La Colla、Paolo La Colla

  DOI：10.1021/jm031147e

  日期：2004.7.1

  Non-nucleoside reverse transcriptase inhibitors (NNRTIs) active against NNRTI-resistant mutants were obtained by introducing two methyl groups at positions 3 and 5 of the benzenesulfonyl moiety of L-737,126 (1) and coupling one to three glycinamide/alaninamide units to its carboxyamide function. In cell-based assays, the new derivatives showed activities against HIV-1 wild type and NNRTI-resistant

  通过在L-737,126的苯磺酰基部分的3和5位上引入两个甲基并将1至3个甘氨酰胺/丙氨酰胺单元与其羧基酰胺偶联，可以获得对NNRTI抗性突变体有活性的非核苷逆转录酶抑制剂（NNRTIs）。功能。在基于细胞的测定中，新衍生物显示出对HIV-1野生型和NNRTI耐药突变体[Y181C，K103N-Y181C和对依非韦伦高度耐药的三重突变体（K103R，V179D，P225H）的活性优于父本的活性。吲哚衍生物1。
• Phenylindoles for the treatment of HIV
  申请人：——

  公开号：US20020193415A1

  公开（公告）日：2002-12-19

  The invention as disclosed herein is a method and composition for the treatment of HIV in humans and other host animals, that includes the administration of an effective HIV treatment amount of a phenylindole as described herein or a pharmaceutically acceptable salt or prodrug thereof, optionally in a pharmaceutically acceptable carrier. The compounds of this invention either possess antiviral (i.e., anti-HIV) activity, or are metabolized to a compound that exhibits such activity.

  本发明公开了一种用于治疗人类和其他宿主动物体内的HIV的方法和组合物，包括根据本文所述的给予有效的HIV治疗量的苯基吲哚或其药学上可接受的盐或前药，可选地在药学上可接受的载体中。本发明的化合物具有抗病毒（即抗HIV）活性，或者经代谢后形成具有该活性的化合物。
• Catalytic Enantioselective Construction of Chiral γ-Azido Nitriles through Nitrile Group-Promoted Electrophilic Reaction of Alkenes
  作者：Yaoyu Liang、Hongtai Huang、Nan Huang、Lihao Liao、Xiaodan Zhao

  DOI：10.1021/acs.orglett.3c02650

  日期：2023.9.15

  construction of enantioenriched γ-azido nitriles through the chiral sulfide-catalyzed asymmetric electrophilic thioazidation of allylic nitriles is disclosed. A wide range of electron-deficient and -rich aryl, heterocyclic aryl, and alkyl substituents are suitable on the substrates of allylic nitriles. The regio-, enantio-, and diastereoselectivities of the reactions are excellent. As versatile platform

  公开了一种通过手性硫化物催化烯丙腈的不对称亲电硫代叠氮化反应构建对映体富集的γ-叠氮腈的有效方法。各种缺电子和富电子芳基、杂环芳基和烷基取代基都适用于烯丙腈的底物。反应的区域选择性、对映选择性和非对映选择性都非常出色。作为通用的平台分子，所获得的手性γ-叠氮腈可以很容易地转化为其他方法不易获得的高附加值手性分子。对照实验表明，烯丙腈基团对于控制反应的反应性和对映选择性非常重要，从而产生广泛的底物范围。
• Copper-Catalyzed Sulfur Alkylation of Sulfenamides with N-Sulfonylhydrazones
  作者：Yidan Han、Yin Yuan、Shutao Qi、Zhi-Kun Zhang、Xiangfei Kong、Junfeng Yang、Junliang Zhang

  DOI：10.1021/acs.orglett.4c01086

  日期：2024.5.10

  compounds in both organic synthesis and pharmaceuticals. In this study, we present a copper-catalyzed sulfur alkylation of sulfenamides with N-sulfonylhydrazones. In contrast to prior findings, hydrazones derived from aldehydes act as donor-type carbene precursors, effectively engaging in coupling with sulfenamides via a copper catalyst, demonstrating exclusive S selectivity. The utility of the protocol was

  磺亚胺是有机合成和制药中有价值的化合物。在这项研究中，我们提出了铜催化的次磺酰胺与N-磺酰腙的硫烷基化反应。与之前的发现相反，由醛衍生的腙充当供体型卡宾前体，通过铜催化剂有效地与次磺酰胺偶联，表现出独特的S选择性。该协议的实用性在快速获得各种亚砜亚胺衍生物方面得到了突出。
• Indolylarylsulfones Bearing Natural and Unnatural Amino Acids. Discovery of Potent Inhibitors of HIV-1 Non-Nucleoside Wild Type and Resistant Mutant Strains Reverse Transcriptase and Coxsackie B4 Virus
  作者：Francesco Piscitelli、Antonio Coluccia、Andrea Brancale、Giuseppe La Regina、Anna Sansone、Cesare Giordano、Jan Balzarini、Giovanni Maga、Samantha Zanoli、Alberta Samuele、Roberto Cirilli、Francesco La Torre、Antonio Lavecchia、Ettore Novellino、Romano Silvestri

  DOI：10.1021/jm801470b

  日期：2009.4.9

  New potent indolylarylsulfone (IAS) HIV-I NNRTIs were obtained by coupling natural and unnatural amino acids to the 2-carboxamide and introducing different electron-withdrawing substituents at position 4 and 5 of the indole nucleus. The new IASs inhibited the HIV-1 replication in human T-lymphocyte (CEM) cells at low/subnanomolar concentration and were weakly cytostatic. Against the mutant L100I, K103N, and Y181C RT HIV-1 strains in CEM cells, sulfones 3, 4, 19, 27, and 31 were comparable to EFV. The new IASs were inhibitors to Coxsackie B4 virus at low micromolar (2-9 mu M) concentrations. Superimposition of PLANTS docked conformations of IASs 19 and 9 revealed different hydrophobic interactions of the 3,5-dimethylphenyl group, for which a staking interaction with Tyr181 aromatic side chain was observed. The binding mode of 19 was not affected by the L100I mutation and was consistent with the interactions reported for the WT strain.