3-propargylamino-benzonitrile | 476303-92-1

• 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: 3-propargylamino-benzonitrile
• 英文别名: 3-(prop-2-ynylamino)benzonitrile
• CAS: 476303-92-1
• 化学式: C₁₀H₈N₂
• mdl: MFCD16661669
• 分子量: 156.187
• InChiKey: GGOJZWQSQXRBQB-UHFFFAOYSA-N

物化性质

• 沸点：
  314.9±27.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  35.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-propargylamino-benzonitrile 、 在 copper(I) iodide 作用下， 以 水 、 乙腈 为溶剂， 反应 3.0h， 以84%的产率得到methyl 7-(4-(11-(4-(((3-cyanophenyl)amino)methyl)-1H-1,2,3-triazol-1-yl)undecanoyl)piperazin-1-yl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate
  参考文献：
  名称：

  Synthesis of Bioactive Complex Small Molecule–Ciprofloxacin Conjugates and Evaluation of Their Antibacterial Activity

  摘要：

  Conjugates between pharmaceuticals and small molecules enable access to a vast chemical space required for the discovery of new lead molecules with modified therapeutic potential. However, the dearth of specific chemical reactions that are capable of functionalizing drugs and bioactive natural products presents a formidable challenge for preparing their conjugates. Here, we report a support-free CuI-nanoparticle-catalyzed strategy for conjugating electron-deficient and electron-rich terminal alkynes with a ciprofloxacin methyl ester. Our conjugation technique exploits the late-stage functionalization of bioactive natural products such as tocopherol, vasicinone, amino acids, and pharmaceuticals such as aspirin and paracetamol to provide conjugates in excellent yields under mild and green conditions. This protocol also enabled the synthesis of (hetero)arene-ciprofloxacin 1,4-disubstituted 1,2,3-triazoles in good yields and high regioselectivities. These synthesized ciprofloxacin conjugates were evaluated in vitro for their antibacterial activity against a panel of relevant bacteria. A significant number of conjugates showed comparable activity against Gram-positive and Gram-negative bacteria. Moreover, some conjugates exhibited less toxicity than ciprofloxacin against two mammalian cell lines, suggesting the utility for the future investigation of these compounds for in vivo efficacy and pharmacokinetic studies.

  DOI：

  10.1021/acscombsci.0c00060
• 作为产物：
  描述：

  N,N-二异丙基乙胺 、 3-溴丙炔 、 间氨基苯甲腈 在 水 、 silica gel 、 dichloromethane ethanol 作用下， 以 甲苯 、 乙酸乙酯 为溶剂， 反应 18.0h， 生成 3-propargylamino-benzonitrile
  参考文献：
  名称：

  Substituted aryl and heteroaryl derivatives, the preparation thereof and the use therof as pharmaceutical compositions

  摘要：

  本发明涉及一种新的取代芳基和杂环芳基衍生物的通式1，其中A，Ar，n，X，Y1，Y2，Y3，Y4，R1和R5如权利要求1中所定义，其前药，互变异构体，立体异构体，其混合物及其盐，特别是其与无机或有机酸或碱的生理可接受盐，具有有价值的性质。因此，上述通式I中R5不含氰基的化合物具有特别的抗血栓作用和选择性因子Xa抑制作用，且具有通常改善的相容性。上述通式I中R5含有氰基的化合物是制备通式I的抗血栓化合物的有价值中间体。

  公开号：

  US20030045712A1

文献信息

• AMIDIN-SUBSTITUIERTE ARYL- UND HETEROARYLDERIVATE MIT ANTITHROMBOTISCHER UND FAKTOR XA-INHIBIERENDER WIRKUNG
  申请人：Boehringer Ingelheim Pharma GmbH & Co.KG

  公开号：EP1404648A1

  公开（公告）日：2004-04-07
• US7005437B2
  申请人：——

  公开号：US7005437B2

  公开（公告）日：2006-02-28
• [DE] AMIDIN-SUBSTITUIERTE ARYL- UND HETEROARYLDERIVATE MIT ANTITHROMBOTISCHER UND FAKTOR XA-INHIBIERENDER WIRKUNG<br/>[EN] AMIDINE SUBSTITUTED ARYL AND HETEROARYL DERIVATIVES WITH AN ANTITHROMBOTIC AND FACTOR XA INHIBITING ACTION<br/>[FR] DERIVES ARYLE ET HETEROARYLE SUBSTITUES PAR UN GROUPE AMIDINE, CES DERIVES POSSEDANT UNE ACTION ANTITHROMBOTIQUE ET UNE ACTION INHIBITRICE SUR LE FACTEUR XA
  申请人：BOEHRINGER INGELHEIM PHARMA

  公开号：WO2003101942A1

  公开（公告）日：2003-12-11

  Die vorliegende Erfindung betrifft neue substituierte Aryl- und Heteroarylderivate der allgemeinen Formel (I) in der A, Ar, n, X, Y1, Y2, Y3, Y4, R1, und R5 wie im Anspruch 1 definiert sind, deren Prodrugs, deren Tautomere, deren Stereoisomere, deren Gemische und deren Salze, insbesondere deren physiologisch vertragliche Salze mit anorganischen oder organischen Säuren oder Basen, welche wertvolle Eigenschaften aufweisen. So weisen die Verbindungen der obigen allgemeinen Formel (I), in denen R5 keine Cyanogruppe enthält, insbesondere eine antithrombotische Wirkung und eine selektive Faktor Xa-inhibierende Wirkung mit allgemein besserer Verträglichkeit auf. Die Verbindungen der obigen allgemeinen Formel (I), in denen R5 eine Cyanogruppe enthalt, stellen wertvolle Zwischenprodukte zur Herstellung der antithrombotischen Verbindungen der allgemeinen Formel (I) dar.
• Synthesis of Bioactive Complex Small Molecule–Ciprofloxacin Conjugates and Evaluation of Their Antibacterial Activity
  作者：Rahul Upadhyay、Rahul Kumar、Manoj Jangra、Rohit Rana、Onkar S. Nayal、Hemraj Nandanwar、Sushil K. Maurya

  DOI：10.1021/acscombsci.0c00060

  日期：2020.9.14

  Conjugates between pharmaceuticals and small molecules enable access to a vast chemical space required for the discovery of new lead molecules with modified therapeutic potential. However, the dearth of specific chemical reactions that are capable of functionalizing drugs and bioactive natural products presents a formidable challenge for preparing their conjugates. Here, we report a support-free CuI-nanoparticle-catalyzed strategy for conjugating electron-deficient and electron-rich terminal alkynes with a ciprofloxacin methyl ester. Our conjugation technique exploits the late-stage functionalization of bioactive natural products such as tocopherol, vasicinone, amino acids, and pharmaceuticals such as aspirin and paracetamol to provide conjugates in excellent yields under mild and green conditions. This protocol also enabled the synthesis of (hetero)arene-ciprofloxacin 1,4-disubstituted 1,2,3-triazoles in good yields and high regioselectivities. These synthesized ciprofloxacin conjugates were evaluated in vitro for their antibacterial activity against a panel of relevant bacteria. A significant number of conjugates showed comparable activity against Gram-positive and Gram-negative bacteria. Moreover, some conjugates exhibited less toxicity than ciprofloxacin against two mammalian cell lines, suggesting the utility for the future investigation of these compounds for in vivo efficacy and pharmacokinetic studies.
• Substituted aryl and heteroaryl derivatives, the preparation thereof and the use therof as pharmaceutical compositions
  申请人：Boehringer Ingelheim Pharma KG

  公开号：US20030045712A1

  公开（公告）日：2003-03-06

  The present invention relates to new substituted aryl and heteroaryl derivatives of general formula 1 wherein A, Ar, n, X, Y 1 , Y 2 , Y 3 , Y 4 , R 1 and R 5 are defined as in claim 1 , the prodrugs, the tautomers, stereoisomers, mixtures thereof and the salts thereof, particularly the physiologically acceptable salts thereof with inorganic or organic acids or bases which have valuable properties. Thus, the compounds of the above general formula I wherein R 5 does not contain a cyano group have, in particular, an antithrombotic effect and a selective factor Xa-inhibiting effect with generally improved compatibility. The compounds of the above general formula I wherein R 5 contains a cyano group are valuable intermediate products for preparing the antithrombotic compounds of general formula I.

  本发明涉及一种新的取代芳基和杂环芳基衍生物，其一般化学式为1，其中A、Ar、n、X、Y1、Y2、Y3、Y4、R1和R5如权利要求书中定义，其前药、互变异构体、立体异构体、它们的混合物及其盐，特别是其与具有有价值性能的无机或有机酸或碱的生理可接受的盐。因此，上述一般式I中的化合物，其中R5不含氰基，具有特别的抗血栓作用和选择性因子Xa抑制作用，并且通常具有改进的相容性。上述一般式I中的化合物，其中R5含有氰基，是制备一般式I抗血栓化合物的有价值的中间体。