pentane-5'-carboxy-(1'-piperidinyl)-carboxamide | 347142-76-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: pentane-5'-carboxy-(1'-piperidinyl)-carboxamide
• 英文别名: 5-oxo-5-(piperidin-1-yl)pentanoic acid；5-Oxo-5-piperidin-1-ylpentanoic acid
• CAS: 347142-76-1
• 化学式: C₁₀H₁₇NO₃
• mdl: MFCD03378721
• 分子量: 199.25
• InChiKey: PVZBZESZLKWJLS-UHFFFAOYSA-N

物化性质

• 沸点：
  411.1±28.0 °C(Predicted)
• 密度：
  1.152±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  pentane-5'-carboxy-(1'-piperidinyl)-carboxamide 在 吖啶 、 bromo Co(III)(dmgH)2py 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 36.0h， 以83%的产率得到1-(piperidin-1-yl)but-3-en-1-one
  参考文献：
  名称：

  羧酸和生物质的光催化化学酶相容脱氢脱羧合成烯烃

  摘要：

  通过温和的化学选择性催化方法将可再生生物质和生物衍生化学品直接转化为有价值的合成中间体，用于有机合成和材料科学应用，在很大程度上仍然难以捉摸。通过利用以前无法实现的反应性和选择性模式，开发与酶促反应兼容的人工催化系统为这一持久挑战提供了协同解决方案。我们在此报告了一种双催化脱氢脱羧反应，该反应是通过光诱导吖啶催化的 O-H 氢原子转移 (HAT) 和钴肟催化的 C-H-HAT 过程的交叉实现的。该反应由容易获得的羧酸产生多种烯烃。

  DOI：

  10.1021/acscatal.9b02951
• 作为产物：
  描述：

  哌啶 、 己二酸酐 以 二氯甲烷 为溶剂， 反应 5.0h， 以95%的产率得到pentane-5'-carboxy-(1'-piperidinyl)-carboxamide
  参考文献：
  名称：

  Polycyclic aromatic compounds as anticancer agents: structure–activity relationships of chrysene and pyrene derivatives

  摘要：

  A large number of diamides and diamines were synthesized using 6-amino chrysene and 1-amino pyrene as starting materials. A structure-activity study with cis-platinum as internal control against animal and human tumor lines was carried out in vitro. This study indicated that the in vitro cytotoxicity toward these lines depends on the functionality present in the molecules. The diamino compounds were found to be more potent than the diamides, and these were equally active irrespective of the end heterocyclic group, whereas the activity of the diamides was strongly dependent on the terminal unit. In general, the diamides containing chrysene as the chromophore were more active than those with a pyrene ring. The size of the end heterocyclic ring, along with the nature of the spacer connecting the polycyclic ring to the heterocyclic ring, seemed to affect the biological activity in certain cell lines. Hemolysis experiments on a lead compound established that it had activities similar to those described for membrane-stabilizing agents. This agent also demonstrated the capacity to produce differentiation in leukemia cell lines. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00297-2

文献信息

• Discovery of memantyl urea derivatives as potent soluble epoxide hydrolase inhibitors against lipopolysaccharide-induced sepsis
  作者：Fangyu Du、Wenjiao Sun、Christophe Morisseau、Bruce D. Hammock、Xuefei Bao、Qiu Liu、Chao Wang、Tan Zhang、Hao Yang、Jun Zhou、Wei Xiao、Zhongbo Liu、Guoliang Chen

  DOI：10.1016/j.ejmech.2021.113678

  日期：2021.11

  Sepsis, a systemic inflammatory response, caused by pathogenic factors including microorganisms, has high mortality and limited therapeutic approaches. Herein, a new soluble epoxide hydrolase (sEH) inhibitor series comprising a phenyl ring connected to a memantyl moiety via a urea or amide linkage has been designed. A preferential urea pharmacophore that improved the binding properties of the compounds

  脓毒症是一种由微生物等致病因素引起的全身炎症反应，死亡率高，治疗方法有限。在此，设计了一种新的可溶性环氧化物水解酶（sEH）抑制剂系列，其包含通过脲或酰胺键连接到美金刚部分的苯环。通过体外和体内生化分析研究，确定了这些系列中可改善化合物结合特性的优先尿素药效基团。分子对接显示， B401中金刚烷基上的3,5-二甲基可以与sEH活性位点疏水口袋上的残基发生范德华相互作用，这可能间接解释了美金刚脲衍生物的体外亚纳摩尔水平活性优于AR- 9281 .其中，化合物B401显着提高了抑制效力，人和鼠的sEH IC 50值分别为0.4 nM和0.5 nM。虽然LPS诱导的脓毒症模型中C57BL/6小鼠的中位生存时间略有增加，但生存率并未达到显着疗效。基于安全性、代谢稳定性、药代动力学和体内功效， B401证明了此类基于美金刚脲的 sEH 抑制剂作为脓毒症治疗药物的潜力。
• Fluorous tagged small molecule microarrays
  作者：Rebecca L. Nicholson、Mark L. Ladlow、David R. Spring

  DOI：10.1039/b712906h

  日期：——

  The affinity fluorous interaction between fluorous tagged small molecules and a fluoroalkyl modified glass surface was shown to facilitate the detection of protein-ligand binding interactions in the fabrication and screening of small molecule microarrays.

  荧光标记的小分子和氟烷基改性的玻璃表面之间的亲和氟相互作用显示出有助于在小分子微阵列的制造和筛选中检测蛋白质-配体结合相互作用。
• Design, synthesis and biological evaluation of novel pyrenyl derivatives as anticancer agents
  作者：Debasish Bandyopadhyay、Jorge L. Sanchez、Adrian M. Guerrero、Fang-Mei Chang、Jose C. Granados、John D. Short、Bimal K. Banik

  DOI：10.1016/j.ejmech.2014.09.072

  日期：2015.1

  Polycyclic aromatic hydrocarbons are widespread in nature with a toxicity range from non-toxic to extremely toxic. A series of pyrenyl derivatives has been synthesized following a four-step strategy where the pyrene nucleus is attached with a basic heterocyclic moiety through a carbon linker. Virtual screening of the physicochemical properties and druggability has been carried out. The cytotoxicity of the compounds (1-8) have been evaluated in vitro against a small panel of human cancer cell lines which includes two liver cancer (HepG2 and Hepa 1-6), two colon cancer (HT-29 and Caco-2) and one each for cervical (HeLa) and breast (MCF-7) cancer cell lines. The IC50 data indicate that compound 6 and 8 are the most effective cytotoxic agents in the present set of pyrenyl derivatives, suggesting that having a 4-carbon linker is more effective than a 5-carbon linker and the presence of amide carbonyl groups in the linker severely reduces the efficacy of the compound. The compounds showed selectivity toward cancer cells at lower doses (<5 mu M) when compared with the normal hepatocytes. The mechanism of action supports the cell death through apoptosis in a caspase-independent manner without cleavage of poly (ADP-ribose) polymerase (PARP), even though the compounds cause plasma membrane morphological changes. The compounds, whether highly cytotoxic or mildly cytotoxic, localize to the membrane of cells. The compounds with either a piperidine ring (6) or an N-methyl piperazine (8) in the side chain were both capable of circumventing the drug resistance in SKOV3-MDR1-M6/6 ovarian cancer cells overexpressing P-glycoprotein. Qualitative structure-activity relationship has also been studied. (C) 2014 Published by Elsevier Masson SAS.
• US7514449B2
  申请人：——

  公开号：US7514449B2

  公开（公告）日：2009-04-07
• [EN] CYCLIC AMINE DERIVATIVE AND PHARMACEUTICAL USE THEREOF<br/>[FR] DÉRIVÉ D'AMINE CYCLIQUE ET UTILISATION PHARMACEUTIQUE ASSOCIÉE<br/>[JA] 環状アミン誘導体及びその医薬用途
  申请人：TORAY INDUSTRIES

  公开号：WO2017131156A1

  公开（公告）日：2017-08-03

  本発明は、レチノイド関連オーファン受容体γアンタゴニスト活性を有し、多発性硬化症若しくは乾癬等の自己免疫疾患又は接触性皮膚炎若しくはアトピー性皮膚炎等のアレルギー性皮膚炎等のアレルギー性疾患に対して治療効果又は予防効果を発揮する新規な化合物を提供することを目的としている。本発明は、下式に代表される環状アミン誘導体又はその薬理学的に許容される塩を提供する。