N¹,N⁴-bis(4-cyanophenyl)terephthalamide | 69489-60-7

• 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: N¹,N⁴-bis(4-cyanophenyl)terephthalamide
• 英文别名: N,N'-bis(4-cyanophenyl)terephthalamide；N,N'-bis-(4-cyanophenyl)terephthalamide；Bis(p-cyanophenyl)terephthalamid；1-N,4-N-bis(4-cyanophenyl)benzene-1,4-dicarboxamide
• CAS: 69489-60-7
• 化学式: C₂₂H₁₄N₄O₂
• 分子量: 366.379
• InChiKey: FGHQBYHTCOSPMT-UHFFFAOYSA-N

物化性质

• 熔点：
  343-346 °C
• 沸点：
  490.2±40.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  106
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N¹,N⁴-bis(4-cyanophenyl)terephthalamide 在 sodium hydrogen sulfide 作用下， 以 N,N-二甲基乙酰胺 、 乙腈 为溶剂， 反应 2.5h， 生成 N,N'-bis[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]terephthalamide dimesylate
  参考文献：
  名称：

  二咪唑啉酰胺对非洲锥虫病的活性

  摘要：

  我们在体外鉴定了几种二咪唑啉单酰胺和二酰胺，它们与喷他脒对罗得西亚布氏锥虫一样有效。所有这些也比喷他脒的细胞毒性更小，但在罗得西亚布氏锥虫感染的小鼠模型中，没有一种比喷他脒更有效。如果存在第二个弱碱官能团，单个咪唑啉可能足以获得高抗锥虫活性。

  DOI：

  10.1016/j.bmcl.2013.12.064
• 作为产物：
  描述：

  对苯二甲酸 在 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 N¹,N⁴-bis(4-cyanophenyl)terephthalamide
  参考文献：
  名称：

  新型化合物的鉴定和结构-活性关系增强了大肠杆菌中抗生素的活性

  摘要：

  在革兰氏阴性细菌中，外排泵能够防止多种抗生素达到有效的细胞浓度。充当外排泵抑制剂（EPI）的小分子佐剂有可能使现有的由于外排机制无效的抗生素恢复活力。通过严格的实验筛选和计算机虚拟筛选的组合，我们最近确定了与膜融合蛋白AcrA相互作用的新型EPI，AcrA是大肠杆菌中AcrAB-TolC外排泵的关键组件。在本文中，我们介绍了围绕先前提到的命中之一NSC 60339（1）的初步优化工作以及结构与活性之间的关系。通过这些努力，我们确定了两种化合物，SLUPP - 225（17小时）和SLUPP - 417（170），它表现出良好的特性，如潜在环境绩效指标大肠杆菌细胞，包括渗透外膜的能力，改进的相对流出的抑制作用1新生霉素的活性的，和增强和红霉素。

  DOI：

  10.1021/acs.jmedchem.7b00453

文献信息

• Aromatic 1,4-DI-Carboxylamides and their use
  申请人：The Genetics Company, Inc.

  公开号：EP1932834A1

  公开（公告）日：2008-06-18

  The invention relates to novel compounds of formula I Wherein X, Y, Z represent independently from one another C or N, n stands for 1, 2, 3, m is 0 or 1, p stands for 0 or an integer from 1 to 6, R1, R2 represent independently from one another hydrogen, a halogen atom, a hydroxyl group, a C1-C3 alkyl group and a C1-C3 alkoxy group, R3 represents, independently from one another if p is not 0, hydrogen, halogen, a C1-C5 linear or branched alkyl, a carboxylyl, a carbomethoxyl, carboethoxyl, a benzyl, an acyl, a hydroxyl, a C1-C4 linear or branched alkoxyl, a trifluoromethyl, a cyano, a morpholino, a 1,3-dioxolyl, an N-acetylamidyl or an amidoyl group, a saturated 5-8 membered ring, a heterocyclic ring, optionally substituted by a C1-C3 alkyl, a hydroxyl or a benzyl group, a C1-C6 alkylsulfonyl, a mono or disubstituted C1-C5 alkyl group, a branched or a cyclic amine, R6 is H or part of a alicyclic,heteroalicyclic ring system, if m is 0 then C represents CF3 or a branched or unbranched C1-C4 alkyl group, if m = 1 then C represents -CH2-O-, -CH2-, -CH2CH2-, -CH2CH2CH2-, -CH2(CH2)CH2- or denotes a chemical bond between N-C or C-C, the CONR6 group may be linked to C either via its carbon or via its nitrogen atom, CYC stands for a by R3 substituted or unsubstituted phenyl, pyridinyl, naphthyl, quinolinyl, isoquinolinyl, isoxaxolinyl, thiophenyl, 1,3,4-thiadiazazolidinyl, furanyl, tetrahydroquinolinyl, tetrahydroisoquinolinyl, morpholinyl, furanyl, cyclohexenyl, and chromen-2-on-yl and its use as a medicament for the treatment of cancer.

  本发明涉及式 I 的新型化合物 其中，X、Y、Z 相互独立地代表 C 或 N，n 代表 1、2、3，m 为 0 或 1，p 代表 0 或 1 至 6 的整数，R1、R2 相互独立地代表氢、卤素原子、羟基、C1-C3 烷基和 C1-C3 烷氧基，R3 相互独立地代表（如果 p 不为 0）氢、卤素原子、C1-C5 直链或支链烷基、羧基、羰基、羧氧羰基、苄基、酰基、C1-C5直链或支链烷基、羧基、甲氧羰基、甲氧羰基、苄基、酰基、羟基、C1-C4直链或支链烷氧基、三氟甲基、氰基、吗啉基、1、3-二氧戊基、N-乙酰氨基或酰胺酰基、饱和的 5-8 位环、杂环（可选择被 C1-C3 烷基、羟基或苄基取代）、C1-C6 烷基磺酰基、C1-C4 直链或支链烷氧基、三氟甲基、氰基、吗啉基、1, 3-二氧戊基、N-乙酰氨基或酰胺酰基R6 是 H 或脂环、杂脂环系统的一部分，如果 m 为 0，则 C 代表 CF3 或支链或未支链的 C1-C4 烷基，如果 m = 1，则 C 代表 -CH2-O-、-CH2-、-CH2CH2-、-CH2CH2CH2-、-CH2(CH2)CH2- 或表示 N-C 或 C-C 之间的化学键、CONR6 基团可以通过碳原子或氮原子与 C 相连，CYC 表示由 R3 取代或未取代的苯基、吡啶基、萘基、喹啉基、异喹啉基、异噁唑啉基、噻吩基、1,3,4-噻二唑烷基、呋喃基、四氢喹啉基、四氢异喹啉基、吗啉基、呋喃基、环己烯基和 2-烯铬基，并用作治疗癌症的药物。
• Synthesis of Analogues of Congo Red and Evaluation of Their Anti-Prion Activity
  作者：Shane Sellarajah、Tamuna Lekishvili、Claire Bowring、Andrew R. Thompsett、Helene Rudyk、Christopher R. Birkett、David R. Brown、Ian H. Gilbert

  DOI：10.1021/jm049922t

  日期：2004.10.1

  No cure as of yet exists for any of the transmissible spongiform encephalopathies. In this paper, we describe the synthesis of analogues of Congo red and evaluation against a cellular model of infection, the SMB (scrapie mouse brain) persistently infected cell line, for their ability to inhibit the infectivity of the abnormal form of prion protein (PrP-res). The compounds have also been tested for their ability to inhibit the polymerization of PrPC by PrP-res. A number of analogues showed inhibition of PrP-res infectivity at nanomolar concentrations. Several analogues show promise; the most active compound, 2a, inhibits the formation of PrP-res in SMB cells with an EC50 of 25-50 nM.
• AROMATIC 1,4-DI-CARBOXYLAMIDES AND THEIR USE
  申请人：Garcia Gabriel

  公开号：US20100204219A1

  公开（公告）日：2010-08-12

  The invention relates to novel compounds of formula (I) wherein X, Y, Z represent independently from one another C or N, n stands for 1, 2, 3, m is 0 or 1, p stands for 0 or an integer from 1 to 6, R 1 , R 2 represent independently from one another hydrogen, a halogen atom, a hydroxyl group, a C 1 -C 3 alkyl group and a C 1 -C 3 alkoxy group, R 3 represents, independently from one another if p is not 0, hydrogen, halogen, a C 1 -C 5 linear or branched alkyl, a carboxylyl, a carbomethoxyl, carboethoxyl, a benzyl, an acyl, a hydroxyl, a C 1 -C 4 linear or branched alkoxyl, a trifluoromethyl, a cyano, a morpholino, a 1,3-dioxolyl, an N-acetylamidyl or an amidoyl group, a saturated 5-8 membered ring, a heterocyclic ring, optionally substituted by a C 1 -C 3 alkyl, a hydroxyl or a benzyl group, a C 1 -C 6 alkylsulfonyl, a mono or disubstituted C 1 -C 5 alkyl group, a branched or a cyclic amine, R 6 is H or part of a alicyclic, heteroalicyclic ring system, if m is 0 then C represents CF 3 or a branched or unbranched C 1 -C 4 alkyl group, if m=1 then C represents —CH 2 —O—, —CH 2 —, —CH 2 CH 2 —, —CH 2 CH 2 CH 2 —, —CH 2 (CH 2 )CH 2 — or denotes a chemical bond between N—C or C—C, the CONR 6 group may be linked to C either via its carbon or via its nitrogen atom, CYC stands for a by R 3 substituted or unsubstituted phenyl, pyridinyl, naphthyl, quinolinyl, isoquinolinyl, isoxaxolinyl, thiophenyl, 1,3,4 -thiadiazazolidinyl, furanyl, tetrahydroquinolinyl, tetrahydroisoquinolinyl, morpholinyl, furanyl, cyclohexenyl, and chromen-2-on-yl and its use as a medicament for the treatment of cancer.
• [EN] COMPOUNDS<br/>[FR] COMPOSES
  申请人：MEDICAL RES COUNCIL

  公开号：WO2005085189A2

  公开（公告）日：2005-09-15

  The present invention relates to compounds of formula (I), or pharmaceutically acceptable salts thereof, wherein X is selected from (II) and (III), Y is selected from SO2NH, CONH, CH=N, CH2NH and CH=CH; R1-5 are each independently selected from H, OH, OR6, CO2H, C02R7, NO2, CN CONR8R9, CONHR10, CO2(CH2)nCO2R11, CO2(CH2)mO(CO)R12, CO2CHR13COR14, CONH(CH2)pCO2R15, CONH(CH2)qO(CO)R16, CONHCHRI7COR18; R6-18 are each independently hydrocarbyl; n, m, p and q are each independently 1, 2, 3 or 4; with the proviso that when X is phenyl, Y is CH=CH, R3 is OH and R1, R4 and R5 are H, R2 is other than COON. Further aspects of the invention relate to the use of such compounds in the preparation of a medicament for the treatment or prevention of transmissible spongiform encephalopathies (TSEs), and pharmaceutical compositions comprising the same.
• [EN] AROMATIC 1,4-DI-CARBOXYLAMIDES AND THEIR USE<br/>[FR] 1,4-DI-CARBOXYLAMIDES AROMATIQUES ET LEUR UTILISATION
  申请人：GENETICS CO INC

  公开号：WO2008071397A1

  公开（公告）日：2008-06-19

  [EN] The invention relates to novel compounds of formula (I) wherein X, Y, Z represent independently from one another C or N, n stands for 1, 2, 3, m is 0 or 1, p stands for 0 or an integer from 1 to 6, R₁, R₂ represent independently from one another hydrogen, a halogen atom, a hydroxyl group, a C₁-C₃ alkyl group and a C₁-C₃ alkoxy group, R₃ represents, independently from one another if p is not 0, hydrogen, halogen, a C₁-C₅ linear or branched alkyl, a carboxylyl, a carbomethoxyl, carboethoxyl, a benzyl, an acyl, a hydroxyl, a C₁-C₄ linear or branched alkoxyl, a trifluoromethyl, a cyano, a morpholino, a 1,3-dioxolyl, an N-acetylamidyl or an amidoyl group, a saturated 5-8 membered ring, a heterocyclic ring, optionally substituted by a C₁-C₃ alkyl, a hydroxyl or a benzyl group, a C₁-C₆ alkylsulfonyl, a mono or disubstituted C₁-C₅ alkyl group, a branched or a cyclic amine, R₆ is H or part of a alicyclic, heteroalicyclic ring system, if m is 0 then C represents CF₃ or a branched or unbranched C₁-C₄ alkyl group, if m = 1 then C represents -CH₂-O-, -CH₂-, -CH₂CH₂-, -CH₂CH₂CH₂-, -CH₂(CH₂)CH₂- or denotes a chemical bond between N-C or C-C, the CONR₆ group may be linked to C either via its carbon or via its nitrogen atom, CYC stands for a by R₃ substituted or unsubstituted phenyl, pyridinyl, naphthyl, quinolinyl, isoquinolinyl, isoxaxolinyl, thiophenyl, 1,3,4-thiadiazazolidinyl, furanyl, tetrahydroquinolinyl, tetrahydroisoquinolinyl, morpholinyl, furanyl, cyclohexenyl, and chromen-2-on-yl and its use as a medicament for the treatment of cancer.
  [FR] L'invention concerne de nouveaux composés de formule (I). X, Y, Z représentent indépendamment les uns des autres C ou N, n représente 1, 2, 3, m représente 0 ou 1, p représente 0 ou un nombre entier compris entre 1 et 6, R1, R2 représentent indépendamment l'un de l'autre hydrogène, un atome d'halogène, un groupe hydroxyle, un groupe alkyle C1-C3 et un groupe alcoxy C1-C3, R3 représente, indépendamment si p n'est pas égal à 0, hydrogène, halogène, un groupe alkyle C1-C5 linéaire ou ramifié, carboxylyle, carbométhoxyle, carboéthoxyle, benzyle, acyle, hydroxyle, alcoxyle C1-C4 linéaire ou ramifié, trifluorométhyle, cyano, morpholino, 1,3-dioxolyle, N-acétylamidyle ou amidoyle, un cycle saturé comprenant de 5-8 chaînons, un cycle hétérocyclique éventuellement substitué par un groupe alkyle C1-C3, hydroxyle ou benzyle, un groupe alkylsulfonyle C1-C6, un groupe alkyle mono ou disubstitué C1-C5, une amine ramifiée ou cyclique, R6 représente H ou une partie d'un système de cycle alicyclique, hétéroalicylcique, si m vaut 0 alors C représente CF3 ou un groupe alkyle C1-C4 ramifié ou non ramifié, si m = 1 alors C représente -CH2-O-, -CH2-, -CH2CH2-, -CH2CH2CH2-, -CH2(CH2)CH2- ou indique une liaison chimique entre N-C ou C-C, le groupe CONR6 peut être lié à C soit par son atome de carbone, soit par son atome d'azote, CYC représente un phényle, pyridinyle, naphthyle, quinolinyle, isoquinolinyle, isoxaxolinyle, thiophényle, 1,3,4-thiadiazazolidinyle, furanyle, tétrahydroquinolinyle, tétrahydroisoquinolinyle, morpholinyle, furanyle, cyclohexényle, et chromén-2-on-yle substiuté ou non substitué par R3. L'invention porte en outre su les utilisations de ces composés en tant que médicament pour le traitement du cancer.