N-苄基-N-甲基-4-哌啶甲酰胺 | 686255-79-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: N-苄基-N-甲基-4-哌啶甲酰胺
• 英文名称: N-methyl-N-(phenylmethyl)-4-piperidinecarboxamide
• 英文别名: 4-(N-methyl-N-benzylcarbamoyl)piperidine；N-benzyl-N-methylpiperidine-4-carboxamide
• CAS: 686255-79-8
• 化学式: C₁₄H₂₀N₂O
• 分子量: 232.326
• InChiKey: KCGJGWKYMLRMOM-UHFFFAOYSA-N

物化性质

• 沸点：
  395.9±41.0 °C(Predicted)
• 密度：
  1.064±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  4-bromo-1-methyl-1-H-pyrrolo[2,3-b]pyridine-3-carbaldehyde 、 N-苄基-N-甲基-4-哌啶甲酰胺 在 tris-(dibenzylideneacetone)dipalladium(0) 、 dipotassium hydrogenphosphate 、 2-二环己膦基-2'-(N,N-二甲胺)-联苯 作用下， 以 1,4-二氧六环 为溶剂， 生成 N-benzyl-1-(3-formyl-1-methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)-N-methylpiperidine-4-carboxamide
  参考文献：
  名称：

  4-Substituted-7-azaindoles bearing a ureidobenzofuranone moiety as potent and selective, ATP-competitive inhibitors of the mammalian target of rapamycin (mTOR)

  摘要：

  A series of 5-ureidobenzofuranones was discovered as potent and selective inhibitors of mTOR with good cellular activity. Molecular modeling studies revealed several hydrogen bond interactions of the ureido group with the enzyme at the ATP-binding site. Furthermore, modeling showed that the ureido group is best situated at C-5 of the benzofuranone. Syntheses of 4-ureido and 5-ureidobenzofuranones are presented. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.02.012
• 作为产物：
  描述：

  4-氯羰酰四氢-吡啶羧酸苄酯 在 氢溴酸 作用下， 以 溶剂黄146 、 甲苯 为溶剂， 反应 4.0h， 生成 N-苄基-N-甲基-4-哌啶甲酰胺
  参考文献：
  名称：

  2,4-Diamino-6,7-dimethoxyquinazolines. 2. 2-(4-Carbamoylpiperidino) derivatives as .alpha.1-adrenoceptor antagonists and antihypertensive agents

  摘要：

  A series of 4-amino-2-(4-carbamoylpiperidino)-6,7-dimethoxyquinazolines (2) were synthesized and evaluated for alpha-adrenoceptor affinity and antihypertensive activity. These compounds displayed high binding affinity (Ki, 10(-9)-10(-10) M) and selectivity for alpha 1-adrenoceptors in vitro, and 12, 14, 21-26, and 29 showed similar potency to prazosin. Compounds 26 and 28 were also shown to be competitive antagonists of the postjunctional, vasoconstrictor action of norepinephrine with no significant activity at prejunctional alpha 2-sites. The high binding affinity for series 2 is rationalized in terms of enhanced basicity of the quinazoline nucleus (pKa's: 12, 7.38; 26, 7.53; prazosin, 6.8) and hydrophobic interactions of the carbamoyl substituents. Molecular mechanics calculations and computer-assisted superimposition suggest that the quinazoline 2-substituents in prazosin and 2 occupy the alpha 1-adrenoceptor site in different manners. Antihypertensive activity was evaluated after oral administration (5 mg/kg) to spontaneously hypertensive rats, and 11, 15, 21, 22, and 26 displayed sustained prazosin-like efficacy at the 6-h time point. The high alpha 1-adrenoceptor affinity demonstrated by series 2 in vitro suggests that these marked, and prolonged, falls in blood pressure result from selective blockade of the alpha 1-mediated vasoconstrictor effects of norepinephrine.

  DOI：

  10.1021/jm00389a007

文献信息

• [EN] LOW MOLECULAR WEIGHT 2,5-DISUBSTITUTED THIOPHENE DERIVATIVES AND USE THEREOF IN THERAPY<br/>[FR] DÉRIVÉS DE THIOPHÈNE 2,5-DISUBSTITUÉS DE FAIBLE POIDS MOLÉCULAIRE ET LEUR UTILISATION EN THÉRAPIE
  申请人：NOVASAID AB

  公开号：WO2009098282A1

  公开（公告）日：2009-08-13

  A compound of formula (I). The compound is useful for the treatment of disorders such as pain, fever, inflammation and cancer. A method for preparing the compound.

  一种化合物的化学式（I）。该化合物可用于治疗疼痛、发热、炎症和癌症等疾病。一种制备该化合物的方法。
• 4-Amino-2-piperidino-quinazolines
  申请人：Pfizer Inc.

  公开号：US04243666A1

  公开（公告）日：1981-01-06

  Regulators of the cardiovascular system and, in particular, in the treatment of hypertension having the formula ##STR1## wherein R is lower alkyl; X, is a 3- or 4-position substituent and is --(CH.sub.2).sub.n CONR.sup.1 R.sup.2, --O(CH.sub.2).sub.n CONR.sup.1 R.sup.2 or ##STR2## wherein n is 0, 1 or 2; R.sup.1 is hydrogen or lower alkyl, and R.sup.2 is lower alkyl; lower alkenyl, lower alkynyl, phenyl, substituted phenyl, C.sub.3 -C.sub.7 cycloalkyl; lower alkyl substituted by phenyl, substituted phenyl, C.sub.3 -C.sub.7 cycloalkyl, halogen, trifluoromethyl, hydroxy, lower alkoxy, lower alkoxycarbonyl, phenoxy, substituted phenoxy or --NR.sup.3 R.sup.4 wherein R.sup.3 and R.sup.4 each represent hydrogen, lower alkyl, lower alkanoyl or lower alkylsulfonyl; with the proviso that any O, N or halogen atom in R.sup.2 is separated by at least 2 carbon atoms from the nitrogen atom to which R.sup.2 is attached; or R.sup.1 and R.sup.2 taken together with the nitrogen atom to which they are attached form a morpholino group optionally substituted by one or two lower alkyl groups, or a 1,2,3,4-tetrahydroisoquinolyl group optionally substituted on the benzene ring portion by one or two lower alkoxy groups; the pharmaceutically acceptable bioprecursors therefor, and the pharmaceutically acceptable acid addition salts thereof.

  心血管系统的调节剂，尤其是治疗高血压的化合物，其化学式为##STR1##其中R为低碳基；X为3-或4-位置取代基，为--(CH.sub.2).sub.n CONR.sup.1 R.sup.2，--O(CH.sub.2).sub.n CONR.sup.1 R.sup.2或##STR2##其中n为0、1或2；R.sup.1为氢或低碳基，R.sup.2为低碳基；低碳烯基，低碳炔基，苯基，取代苯基，C.sub.3-C.sub.7环烷基；被苯基，取代苯基，C.sub.3-C.sub.7环烷基，卤素，三氟甲基，羟基，低碳基氧，低碳基氧羰基，苯氧基，取代苯氧基或--NR.sup.3 R.sup.4，其中R.sup.3和R.sup.4各代表氢，低碳基，低碳基酰基或低碳基磺酰基；但要求R.sup.2中的任何O、N或卤素原子与R.sup.2连接的氮原子之间至少相隔2个碳原子；或R.sup.1和R.sup.2与它们连接的氮原子一起形成一个吗啡啶基团，可选择地被一个或两个低碳基取代，或一个1,2,3,4-四氢异喹啉基团，可选择地在苯环部分上被一个或两个低碳基氧基取代；其药学上可接受的生物前体，以及其药学上可接受的酸加合物盐。
• Novel pyridine derivatives
  申请人：Bur Daniel

  公开号：US20070043081A1

  公开（公告）日：2007-02-22

  The invention relates to novel pyridine derivatives and related compounds and their use as active ingredients in the preparation of pharmaceutical compositions. The invention also concerns related aspects including processes for the preparation of the compounds, pharmaceutical compositions containing one or more of those compounds and especially their use as neurohormonal antagonists.

  本发明涉及新型吡啶衍生物及相关化合物，以及它们作为制备药物组合物中的活性成分的用途。本发明还涉及相关方面，包括制备化合物的过程，含有这些化合物中的一个或多个的药物组合物，特别是它们作为神经荷尔蒙拮抗剂的用途。
• Design, synthesis, and biological evaluation of novel piperidine-4-carboxamide derivatives as potent CCR5 inhibitors
  作者：Suwen Hu、Quan Gu、Zhilong Wang、Zhiyong Weng、Yunrui Cai、Xiaowu Dong、Yongzhou Hu、Tao Liu、Xin Xie

  DOI：10.1016/j.ejmech.2013.11.013

  日期：2014.1

  Based on a putative 'Y shape' pharmacophore model of CCR5 inhibitors, a series of novel piperidine-4-carboxamide derivatives were designed and synthesized using a group-reverse strategy. Among synthesized target compounds, 16g (IC50 = 25.73 nM) and 16i (IC50 = 25.53 nM) showed equivalent inhibitory activity against CCR5 to that of the positive control maraviroc (IC50 = 25.43 nM) in calcium mobilization assay. Selected compounds were further tested for their antiviral activity in HIV-1 single cycle assay. Two compounds, 16g and 16i, displayed antiviral activity with IC50 values of 73.01 nM and 94.10 nM, respectively. Additionally, the pharmacokinetic properties and inhibitory potency against hERG of 16g were evaluated, providing a foundation for ongoing optimization. (C) 2013 Elsevier Masson SAS. All rights reserved.
• MMP-13 selective isonipecotamide α-sulfone hydroxamates
  作者：Stephen A. Kolodziej、Susan L. Hockerman、Gary A. DeCrescenzo、Joseph J. McDonald、Debbie A. Mischke、Grace E. Munie、Theresa R. Fletcher、Nathan Stehle、Craig Swearingen、Daniel P. Becker

  DOI：10.1016/j.bmcl.2010.04.111

  日期：2010.6

  A series of N-aryl isonipecotamide alpha-sulfone hydroxamate derivatives has been prepared utilizing a combination of solution-phase and resin-bound library technologies to afford compounds that are potent and highly selective for MMP-13. (C) 2010 Elsevier Ltd. All rights reserved.