4-(3,4-dinitrobenzyl)piperidine | 1254229-44-1

• 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: 4-(3,4-dinitrobenzyl)piperidine
• 英文别名: 1-(3,4-dinitrobenzyl)piperidine；1-(3,4-Dinitrobenzyl)piperidine；1-[(3,4-dinitrophenyl)methyl]piperidine
• CAS: 1254229-44-1
• 化学式: C₁₂H₁₅N₃O₄
• 分子量: 265.269
• InChiKey: SFPGFFDTDYZFFR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  94.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(3,4-dinitrobenzyl)piperidine 在 5%-palladium/activated carbon 、 氢气 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 123.0h， 生成 5-[6-(piperidin-1-ylmethyl)-1H-benzimidazol-2-yl]-1H-pyrazol-4-amine
  参考文献：
  名称：

  Design, synthesis, quantum chemical studies and biological activity evaluation of pyrazole–benzimidazole derivatives as potent Aurora A/B kinase inhibitors

  摘要：

  Novel pyrazole-benzimidazole derivatives have been designed and synthesized. The entire target compounds were determined against cancer cell lines U937, K562, A549, LoVo and HT29 and were screened for Aurora A/B kinase inhibitory activity in vitro. The compounds 7a, 7b, 7i, 7k and 7l demonstrated significant cancer cell lines and Aurora A/B kinase inhibitory activities. Molecular modeling studies suggested the derivatives have bound in the active site of Aurora A kinase through the formation of four hydrogen bonds. Quantum chemical studies were carried out on these compounds to understand the structural features essential for activity. The cellular activity of 7k was also tested by immunofluorescence. (C) 2013 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2013.04.039
• 作为产物：
  描述：

  3,4-二硝基苯甲酸 在 sodium tetrahydroborate 、 氯化亚砜 、 三氟化硼乙醚 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 4-(3,4-dinitrobenzyl)piperidine
  参考文献：
  名称：

  Design, synthesis, quantum chemical studies and biological activity evaluation of pyrazole–benzimidazole derivatives as potent Aurora A/B kinase inhibitors

  摘要：

  Novel pyrazole-benzimidazole derivatives have been designed and synthesized. The entire target compounds were determined against cancer cell lines U937, K562, A549, LoVo and HT29 and were screened for Aurora A/B kinase inhibitory activity in vitro. The compounds 7a, 7b, 7i, 7k and 7l demonstrated significant cancer cell lines and Aurora A/B kinase inhibitory activities. Molecular modeling studies suggested the derivatives have bound in the active site of Aurora A kinase through the formation of four hydrogen bonds. Quantum chemical studies were carried out on these compounds to understand the structural features essential for activity. The cellular activity of 7k was also tested by immunofluorescence. (C) 2013 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2013.04.039

文献信息

• [EN] PYRAZOLYLBENZO[D]IMIDAZOLE DERIVATIVES<br/>[FR] DÉRIVÉS DE PYRAZOLYLBENZO[D]IMIDAZOLE
  申请人：CELON PHARMA SA

  公开号：WO2014141015A1

  公开（公告）日：2014-09-18

  A compound represented by the general Formula (I), whereinhydrogen atoms shown as attached to pyrazole and benzimidazole rings are attached to one of nitrogen atoms of the pyrazole or benzimidazole ring, respectively; R1 represents -X-Q-P, wherein X is absent or represents –CH2-, –C(O)-, or –C(O)NH-(CH2)k-, wherein k is 0, 1 or 2; Q is selected from the group consisting of Q1, Q2, Q3, Q4 and Q5; P is absent or represents straight-or branched-chain C1-C3 alkyl, –(CH2)l-NR2R3, or–(CH2)m-C(O)-NR2R3, wherein l and m independently of each other represent 0, 1 or 2, with the proviso that when B in Q1 represents oxygen atom, then P is absent;and R2and R3 independently represent C1 or C2 alkyl, or R2 and R3 together with nitrogen atom to which they are both attached form a 6- membered saturated heterocyclicring, wherein one of carbon atoms can be replaced with oxygen, -NH-or –N(C1-C2)alkyl-; and acid addition salts thereof. The compound can be useful in the treatment of cancer diseases. (I)

  化合物的一般公式（I）表示，其中作为连接到吡唑和苯并咪唑环的氢原子分别连接到吡唑或苯并咪唑环的氮原子之一；R1表示-X-Q-P，其中X不存在或表示-CH2-，-C(O)-或-C(O)NH-(CH2)k-，其中k为0、1或2；Q从Q1、Q2、Q3、Q4和Q5组成的群体中选择；P不存在或表示直链或支链C1-C3烷基，-(CH2)l-NR2R3，或-(CH2)m-C(O)-NR2R3，其中l和m独立地表示0、1或2，但当Q1中的B表示氧原子时，P不存在；R2和R3独立地表示C1或C2烷基，或R2和R3与它们都连接的氮原子一起形成一个6-成员饱和杂环，其中一个碳原子可以被氧、-NH-或-N(C1-C2)烷基取代；以及其酸盐。该化合物可用于治疗癌症疾病。（I）
• PYRAZOLYLBENZO[D]IMIDAZOLE DERIVATIVES
  申请人：CELON PHARMA S.A.

  公开号：US20160039794A1

  公开（公告）日：2016-02-11

  A compound represented by the general Formula (I), wherein hydrogen atoms shown as attached to pyrazole and benzimidazole rings are attached to one of nitrogen atoms of the pyrazole or benzimidazole ring, respectively; R 1 represents —X-Q-P, wherein X is absent or represents —CH 2 —, —C(O)—, or —C(O)NH—(CH 2 ) k —, wherein k is 0, 1 or 2; Q is selected from the group consisting of Q1, Q2, Q3, Q4 and Q5; P is absent or represents straight- or branched-chain C1-C3 alkyl, —(CH 2 ) l —NR 2 R 3 , or —(CH 2 ) m —C(O)—NR 2 R 3 , wherein l and m independently of each other represent 0, 1 or 2, with the proviso that when B in Q1 represents oxygen atom, then P is absent; and R 2 and R 3 independently represent C1 or C2 alkyl, or R 2 and R 3 together with nitrogen atom to which they are both attached form a 6-membered saturated heterocyclic ring, wherein one of carbon atoms can be replaced with oxygen, —NH—or —N(C1-C2)alkyl-; and acid addition salts thereof. The compound can be useful in the treatment of cancer diseases. (I)

  化合物的通式（I）表示，其中连接到吡唑和苯并咪唑环的氢原子分别连接到吡唑或苯并咪唑环的一个氮原子上；R1表示-X-Q-P，其中X不存在或表示-CH2-，-C（O）-或-C（O）NH-（CH2）k-，其中k为0、1或2；Q从Q1、Q2、Q3、Q4和Q5组成的群体中选择；P不存在或表示直链或支链C1-C3烷基，-（CH2）l-NR2R3或-（CH2）m-C（O）-NR2R3，其中l和m独立地表示0、1或2，但是当Q1中的B表示氧原子时，P不存在；R2和R3独立地表示C1或C2烷基，或者R2和R3与它们都连接的氮原子一起形成一个6元饱和杂环，其中一个碳原子可以被氧、-NH-或-N（C1-C2）烷基取代；以及它的酸加成盐。该化合物可用于治疗癌症。
• US9776988B2
  申请人：——

  公开号：US9776988B2

  公开（公告）日：2017-10-03
• Design, synthesis, quantum chemical studies and biological activity evaluation of pyrazole–benzimidazole derivatives as potent Aurora A/B kinase inhibitors
  作者：Youguang Zheng、Ming Zheng、Xin Ling、Yi Liu、Yunsheng Xue、Lin An、Ning Gu、Min Jin

  DOI：10.1016/j.bmcl.2013.04.039

  日期：2013.6

  Novel pyrazole-benzimidazole derivatives have been designed and synthesized. The entire target compounds were determined against cancer cell lines U937, K562, A549, LoVo and HT29 and were screened for Aurora A/B kinase inhibitory activity in vitro. The compounds 7a, 7b, 7i, 7k and 7l demonstrated significant cancer cell lines and Aurora A/B kinase inhibitory activities. Molecular modeling studies suggested the derivatives have bound in the active site of Aurora A kinase through the formation of four hydrogen bonds. Quantum chemical studies were carried out on these compounds to understand the structural features essential for activity. The cellular activity of 7k was also tested by immunofluorescence. (C) 2013 Published by Elsevier Ltd.