2-异硫代氰酰基-4-甲基吡啶 | 22400-44-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 2-异硫代氰酰基-4-甲基吡啶
• 英文名称: 2-isothiocyanato-4-methylpyridine
• CAS: 22400-44-8
• 化学式: C₇H₆N₂S
• 分子量: 150.204
• InChiKey: RHIXRRXYFRTOFX-UHFFFAOYSA-N

物化性质

• 沸点：
  289.8±28.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  57.3
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  N-(三氟甲基苯基)乙二胺 、 2-异硫代氰酰基-4-甲基吡啶 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 1-(4-Methylpyridin-2-yl)-3-[2-[3-(trifluoromethyl)anilino]ethyl]thiourea
  参考文献：
  名称：

  4-(3-Chloro-5-(trifluoromethyl)pyridin-2-yl)-N-(4-methoxypyridin-2-yl)piperazine-1-carbothioamide (ML267), a Potent Inhibitor of Bacterial Phosphopantetheinyl Transferase That Attenuates Secondary Metabolism and Thwarts Bacterial Growth

  摘要：

  4'-Phosphopantetheinyl transferases (PPTases) catalyze a post-translational modification essential to bacterial cell viability and virulence. We present the discovery and medicinal chemistry optimization of 2-pyridinyl-N-(4-aryl)-piperazine-1-carbothioamides, which exhibit submicromolar inhibition of bacterial Sfp-PPTase with no activity toward the human orthologue. Moreover, compounds within this class possess antibacterial activity in the absence of a rapid cytotoxic response in human cells. An advanced analogue of this series, ML267 (55), was found to attenuate production of an Sfp-PPTase-dependent metabolite when applied to Bacillus subtilis at sublethal doses. Additional testing revealed antibacterial activity against methicillin-resistant Staphylococcus aureus, and chemical genetic studies implicated efflux as a mechanism for resistance in Escherichia coli. Additionally, we highlight the in vitro absorption, distribution, metabolism; and excretion and in vivo pharmacokinetic profiles of compound 55 to further demonstrate the potential utility of this small-molecule inhibitor.

  DOI：

  10.1021/jm401752p
• 作为产物：
  描述：

  在 三光气 作用下， 以 氯仿 为溶剂， 反应 4.5h， 生成 2-异硫代氰酰基-4-甲基吡啶
  参考文献：
  名称：

  使用三光气和助溶剂简便而多功能地合成烷基和芳基异硫氰酸酯

  摘要：

  摘要 以(CH3)2CO-CS2 为共溶剂，三光气为脱氢硫化剂，开发了一种温和高效的二硫代氨基甲酸酯将烷基胺和芳基胺转化为异硫氰酸酯的方法。与报道的方法相比，高产率、温和的反应条件和优异的官能团兼容性使其成为制备异硫氰酸酯的通用合成方法。[本文提供补充材料。访问出版商的 Synthetic Communications® 在线版，获取以下免费补充资源：完整的实验和光谱细节。] 图形摘要

  DOI：

  10.1080/00397911.2013.783600

文献信息

• Microwave-assisted synthesis of novel benzodifuran-based bis(N-(het)arylthiazol-2-amine) derivatives and their antibacterial and antimycobacterial activities
  作者：N. H. Kumar Baba、Dongamanti Ashok、Boddu Ananda Rao、Madderla Sarasija、Nandula Y. S. Murthy

  DOI：10.1007/s10593-018-2323-x

  日期：2018.6

  A new series of 4,4'-(3,5-diphenethylbenzo[1,2-b:5,4-b']difuran-2,6-diyl)bis(N-(het)arylthiazol-2-amine) derivatives have been synthesized from 1,1'-(3,5-diphenethylbenzo[1,2-b:5,4-b']difuran-2,6-diyl)diethanone O,O'-diacetyl dioxime and substituted isothiocyanates under conventional and microwave irradiation conditions. The obtained products were subjected to in vitro antibacterial and antimycobacterial

  新系列的4,4'-（3,5-二苯乙基苯并[1,2- b：5,4 - b ']二呋喃-2,6-二基）双（N-（杂）芳基噻唑-2-胺）衍生物已被从合成1,1' - （3,5-二diphenethylbenzo [1,2 b：5,4- b “]二呋喃-2,6-二基）二乙酮ø，ö ”二乙酰基二肟和取代的异硫氰酸酯下常规和微波辐射条件。对获得的产物进行体外抗菌和抗分枝杆菌活性测试。一些化合物对枯草芽孢杆菌（+ ve）和铜绿假单胞菌具有显着的抗菌活性（-ve）菌株和对牛分枝杆菌菌株的抗分枝杆菌活性。
• [EN] HETEROCYCLIC COMPOUNDS AND THEIR USE FOR TREATMENT OF HELMINTHIC INFECTIONS AND DISEASES<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES ET LEUR UTILISATION POUR LE TRAITEMENT DE MALADIES ET INFECTIONS HELMINTHIQUES
  申请人：CELGENE CORP

  公开号：WO2022087326A1

  公开（公告）日：2022-04-28

  Provided herein are Heterocyclic Compounds of formula (I), formula (II), formula (III), formula (IlIa), formula (Mb), formula (IIIc), formula (Hid), formula (IV), formula (IVa), formula (IVb), and formula (IVc), and pharmaceutically acceptable salts, tautomers, isotopologues, and stereoisomers thereof, compositions comprising an effective amount of a Heterocyclic Compound of formula (I), formula (II), formula (III), formula (IlIa), formula (Mb), formula (IIIc), formula (Hid), formula (IV), formula (IVa), formula (IVb), and formula (IVc), and methods for treating or preventing animal and human filarial worm infections and diseases.

  本文提供了公式(I)、公式(II)、公式(III)、公式(IIIa)、公式(Mb)、公式(IIIc)、公式(Hid)、公式(IV)、公式(IVa)、公式(IVb)和公式(IVc)的杂环化合物，以及其药学上可接受的盐、互变异构体、同位素拓扑异构体和立体异构体，包含有效量的公式(I)、公式(II)、公式(III)、公式(IIIa)、公式(Mb)、公式(IIIc)、公式(Hid)、公式(IV)、公式(IVa)、公式(IVb)和公式(IVc)的杂环化合物的组合物，以及用于治疗或预防动物和人类丝虫感染和疾病的方法。
• Facile and Versatile Synthesis of Alkyl and Aryl Isothiocyanates by Using Triphosgene and CoSolvent
  作者：Pengfei Liu、Chunyan Li、Jingwei Zhang、Xiaoyong Xu

  DOI：10.1080/00397911.2013.783600

  日期：2013.12.17

  efficient method for the conversion of alkyl and aryl amines to isothiocyanates via dithiocarbamates has been developed using (CH3)2CO-CS2 as co-solvent and triphosgene as dehydrosulfurization reagent. High yields, mild reaction conditions and excellent functional group compatibility make it become a versatile synthetic method for the preparation of isothiocyanates compared with reported methods. [Supplementary

  摘要 以(CH3)2CO-CS2 为共溶剂，三光气为脱氢硫化剂，开发了一种温和高效的二硫代氨基甲酸酯将烷基胺和芳基胺转化为异硫氰酸酯的方法。与报道的方法相比，高产率、温和的反应条件和优异的官能团兼容性使其成为制备异硫氰酸酯的通用合成方法。[本文提供补充材料。访问出版商的 Synthetic Communications® 在线版，获取以下免费补充资源：完整的实验和光谱细节。] 图形摘要
• 4-(3-Chloro-5-(trifluoromethyl)pyridin-2-yl)-<i>N</i>-(4-methoxypyridin-2-yl)piperazine-1-carbothioamide (ML267), a Potent Inhibitor of Bacterial Phosphopantetheinyl Transferase That Attenuates Secondary Metabolism and Thwarts Bacterial Growth
  作者：Timothy L. Foley、Ganesha Rai、Adam Yasgar、Thomas Daniel、Heather L. Baker、Matias Attene-Ramos、Nicolas M. Kosa、William Leister、Michael D. Burkart、Ajit Jadhav、Anton Simeonov、David J. Maloney

  DOI：10.1021/jm401752p

  日期：2014.2.13

  4'-Phosphopantetheinyl transferases (PPTases) catalyze a post-translational modification essential to bacterial cell viability and virulence. We present the discovery and medicinal chemistry optimization of 2-pyridinyl-N-(4-aryl)-piperazine-1-carbothioamides, which exhibit submicromolar inhibition of bacterial Sfp-PPTase with no activity toward the human orthologue. Moreover, compounds within this class possess antibacterial activity in the absence of a rapid cytotoxic response in human cells. An advanced analogue of this series, ML267 (55), was found to attenuate production of an Sfp-PPTase-dependent metabolite when applied to Bacillus subtilis at sublethal doses. Additional testing revealed antibacterial activity against methicillin-resistant Staphylococcus aureus, and chemical genetic studies implicated efflux as a mechanism for resistance in Escherichia coli. Additionally, we highlight the in vitro absorption, distribution, metabolism; and excretion and in vivo pharmacokinetic profiles of compound 55 to further demonstrate the potential utility of this small-molecule inhibitor.