N-cyclohexylquinoline-2-carboxamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: N-cyclohexylquinoline-2-carboxamide
• 化学式: C₁₆H₁₈N₂O
• 分子量: 254.332
• InChiKey: ZSEQJGCPYSCJKE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-cyclohexylquinoline-2-carboxamide 在 sodium azide 、 三氯氧磷 作用下， 反应 9.0h， 以76%的产率得到2-(1-cyclohexyl-1H-tetrazol-5-yl)quinoline
  参考文献：
  名称：

  四唑-杂环杂化物的合成、生物学评价和计算机研究

  摘要：

  摘要 为了开发新的先导分子，合成并表征了噻吩、吡啶和喹啉四唑等四唑杂环杂化物的三种不同化学实体。研究了生物学评价，例如体外抗微生物和抗炎活性。此外，还研究了诸如分子对接（使用 COX-1、COX-2 和 3TTZ）、DFT 计算、分子静电势 (MEP) 和 ADME 等计算机研究。

  DOI：

  10.1016/j.molstruc.2018.07.114
• 作为产物：
  描述：

  methyl N-cyclohexyloxamate 在 氢氧化钾 、 sodium persulfate 、 硫酸 、 silver nitrate 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 31.0h， 生成 N-cyclohexylquinoline-2-carboxamide
  参考文献：
  名称：

  Coppa, Fausta; Fontana, Francesca; Lazzarini, Edoardo, Heterocycles, 1993, vol. 36, # 12, p. 2687 - 2696

  摘要：

  DOI：

文献信息

• Pd(<scp>ii</scp>)-Catalyzed gamma-C(sp³)–H alkynylation of amides: selective functionalization of R chains of amides R¹C(O)NHR
  作者：Vinod G. Landge、Ayisha Parveen、Avanashiappan Nandakumar、Ekambaram Balaraman

  DOI：10.1039/c8cc03445a

  日期：——

  of R chains of amides R1C(O)NHR, a fundamental class of synthetic substrates, has not been accomplished to date. Here, the first example of palladium(II)-catalyzed alkynylation of an unactivated gamma C(sp3)–H bond of alkyl amides (cyclic, linear, and amino acids) is reported. The kinetic experiment shows that the rate of the reaction depends on the coupling partners and the amides. Late-stage diversification

  到目前为止，尚未完成酰胺R 1 C（O）NHR的R链的C链C（sp 3）-H键的炔基化反应。在此，报道了钯（II）催化烷基酰胺（环状，线性和氨基酸）的未活化γC（sp 3）-H键的炔基化反应的第一个例子。动力学实验表明，反应速率取决于偶联伙伴和酰胺。通过利用胺和炔烃官能团开发了烷基化酰胺的后期多样化产品。
• PALLADIUM (II)-CATALYZED gammaC(SP3)-H ALKYNYLATION OF AMINE2
  申请人：Council of Scientific & Industrial Research

  公开号：US20200317615A1

  公开（公告）日：2020-10-08

  The present invention relates to a Palladium (II)-catalyzed C(sp 3 )—H alkynylation of amines using picolinamide as directing group. The developed alkynylation strategy is simple, efficient, and tolerant of various ring size including five to eight member cyclic, quaternary amines, and N-heterocyclic motifs.

  本发明涉及一种钯(II)催化的氨基C(sp3)—H炔基化反应，使用吡啶甲酰胺作为定向基团。所开发的炔基化策略简单、高效，并且能容忍包括五至八元环、季铵氨基和N-杂环基团在内的各种环大小。
• Synthesis of cis-3-arylated cycloalkylamines through palladium-catalyzed methylene sp3 carbon–hydrogen bond activation
  作者：Atsushi Seki、Yoshiaki Takahashi、Toshiaki Miyake

  DOI：10.1016/j.tetlet.2014.03.075

  日期：2014.4

  Methylene sp3 carbon–hydrogen bond activation of N-picolinoylcycloalkylamines provides a useful method for synthesizing cis-3-arylated cycloalkylamine derivatives. Pd(II) species catalyzed the γ-arylation of N-picolinoylcycloalkylamines with aryl iodides in the presence of silver carbonate to afford cis-3-arylated N-picolinoylalkylamines in up to 87% yield. Hydrolysis of the amide linkage to give the

  N-吡啶甲基环烷基胺的亚甲基sp 3碳氢键活化为合成顺式-3-芳基化环烷基胺衍生物提供了一种有用的方法。在碳酸银存在下，Pd（II）催化N-吡啶基环烷基胺与芳基碘化物的γ-芳基化反应，以高达87％的收率提供顺式-3-芳基化N-吡啶基烷基胺。还证明了酰胺键的水解以给出相应的顺式-3-芳基化的环烷基胺。
• Visible-light mediated carbamoyl radical addition to heteroarenes
  作者：Ashique Hussain Jatoi、Govind Goroba Pawar、Frédéric Robert、Yannick Landais

  DOI：10.1039/c8cc08326f

  日期：——

  The generation of carbamoyl radicals, followed by their addition to heteroarenes, was performed under mild conditions through a metal-free photocatalyzed decarboxylation of oxamic acids. The process has been applied to the carbamoylation of heteroaromatic bases using α-aminoacid-derived oxamic acids, leading to the corresponding amides without racemization.

  氨基甲酰基自由基的产生，然后将它们加到杂芳烃中，是在温和的条件下通过无金属的草酸的光催化脱羧反应进行的。该方法已被用于使用α-氨基酸衍生的草酰胺酸对杂芳族碱进行氨基甲酰基化，从而得到相应的酰胺而没有外消旋化作用。
• Investigating the Spectrum of Biological Activity of Substituted Quinoline-2-Carboxamides and Their Isosteres
  作者：Tomas Gonec、Pavel Bobal、Josef Sujan、Matus Pesko、Jiahui Guo、Katarina Kralova、Lenka Pavlacka、Libor Vesely、Eva Kreckova、Jiri Kos、Aidan Coffey、Peter Kollar、Ales Imramovsky、Lukas Placek、Josef Jampilek

  DOI：10.3390/molecules17010613

  日期：——

  In this study, a series of thirty-five substituted quinoline-2-carboxamides and thirty-three substituted naphthalene-2-carboxamides were prepared and characterized. They were tested for their activity related to the inhibition of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. Primary in vitro screening of the synthesized compounds was also performed against four mycobacterial species. N-Cycloheptylquinoline-2-carboxamide, N-cyclohexylquinoline-2-carboxamide and N-(2-phenylethyl)quinoline-2-carboxamide showed higher activity against M. tuberculosis than the standards isoniazid or pyrazinamide and 2-(pyrrolidin-1-ylcarbonyl)quinoline and 1-(2-naphthoyl)pyrrolidine expressed higher activity against M. kansasii and M. avium paratuberculosis than the standards isoniazid or pyrazinamide. The most effective antimycobacterial compounds demonstrated insignificant toxicity against the human monocytic leukemia THP-1 cell line. The PET-inhibiting activity expressed by IC50 value of the most active compound N-benzyl-2-naphthamide was 7.5 μmol/L. For all compounds, the structure-activity relationships are discussed.

  本研究制备并鉴定了一系列 35 种取代的喹啉-2-羧酰胺和 33 种取代的萘-2-羧酰胺。对它们抑制菠菜叶绿体光合电子传递（PET）的活性进行了测试。还对合成的化合物进行了针对四种霉菌的体外初筛。N-环庚基喹啉-2-甲酰胺、N-环己基喹啉-2-甲酰胺和 N-(2-苯基乙基)喹啉-2-甲酰胺对结核杆菌的活性高于标准异烟肼。与标准异烟肼或吡嗪酰胺相比，N-环己基喹啉-2-甲酰胺和 N-(2-苯基乙基)喹啉-2-甲酰胺对结核杆菌的活性更高；与标准异烟肼或吡嗪酰胺相比，2-(吡咯烷-1-羰基)喹啉和 1-(2-萘甲酰基)吡咯烷对堪萨斯疫霉菌和副结核杆菌的活性更高。最有效的抗霉菌化合物对人类单核细胞白血病 THP-1 细胞系的毒性很小。最有效化合物 N-苄基-2-萘甲酰胺的 PET 抑制活性（以 IC50 值表示）为 7.5 μmol/L。本文讨论了所有化合物的结构-活性关系。