N-(3-bromopropyl)-2-naphthamide | 145798-55-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(3-bromopropyl)-2-naphthamide
• 英文别名: N-(3-bromopropyl)naphthalene-2-carboxamide
• CAS: 145798-55-6
• 化学式: C₁₄H₁₄BrNO
• mdl: MFCD11133400
• 分子量: 292.175
• InChiKey: QGHKBLSREWXWAG-UHFFFAOYSA-N

物化性质

• 沸点：
  490.6±28.0 °C(Predicted)
• 密度：
  1.390±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.214
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(3-bromopropyl)-2-naphthamide 、 1-(4-chlorophenyl)piperazine dihydrochloride 在 三乙胺 作用下， 以 二甲基亚砜 为溶剂， 以44%的产率得到N-(3-(4-(4-chlorophenyl)piperazin-1-yl)propyl)-2-naphthamide
  参考文献：
  名称：

  Design, synthesis and docking study of 4-arylpiperazine carboxamides as monoamine neurotransmitters reuptake inhibitors

  摘要：

  Rational drug design method has been used to generate 4-arylpiperazine carboxamides in an effort to develop safer, more potent and effective monoamine neurotransmitters reuptake inhibitors. Out of twenty-seven synthesized compounds, compound 9 displayed potent monoamine neurotransmitter reuptake inhibitory activity against HEK cells transfected with hSERT or hNET. A Surflex-Dock docking model of 9 was also studied.

  DOI：

  10.1016/j.bmc.2018.06.043
• 作为产物：
  描述：

  3-溴丙胺氢溴酸盐 、 2-萘甲酸 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以63%的产率得到N-(3-bromopropyl)-2-naphthamide
  参考文献：
  名称：

  신규한 카복사마이드 유도체 염 및 그 용도

  摘要：

  This invention relates to a novel carbazomide derivative salt having therapeutic effects for mental disorders, and its use. The compound of chemical formula 1 or a pharmaceutically acceptable salt thereof can treat or prevent mental disorders such as depression, anxiety disorders, panic disorders, obsessive-compulsive disorders, phobias, and attention deficit hyperactivity disorder. It can increase compliance, have minimal side effects, and have a therapeutic effect for mental disorders by effectively inhibiting the reuptake of serotonin, norepinephrine, or dopamine.

  公开号：

  KR101784964B1

文献信息

• Synthesis and Structure–Activity Relationship Investigation of Adenosine-Containing Inhibitors of Histone Methyltransferase DOT1L
  作者：Justin L. Anglin、Lisheng Deng、Yuan Yao、Guobin Cai、Zhen Liu、Hong Jiang、Gang Cheng、Pinhong Chen、Shuo Dong、Yongcheng Song

  DOI：10.1021/jm300917h

  日期：2012.9.27

  Histone3-lysine79 (H3K79) methyltransferase DOT1L has been found to be a drug target for acute leukemia with MLL (mixed lineage leukemia) gene translocations. A total of 55 adenosine-containing compounds were designed and synthesized, among which several potent DOT1L inhibitors were identified with Ki values as low as 0.5 nM. These compounds also show high selectivity (>4500-fold) over three other histone methyltransferases

  组蛋白 3-赖氨酸 79 (H3K79) 甲基转移酶 DOT1L 已被发现是具有 MLL（混合谱系白血病）基因易位的急性白血病的药物靶点。总共设计和合成了 55 种含腺苷的化合物，其中鉴定了几种有效的 DOT1L 抑制剂，K i值低至 0.5 nM。与其他三种组蛋白甲基转移酶相比，这些化合物还显示出高选择性（> 4500 倍）。讨论了这些化合物对 DOT1L 的抑制活性的构效关系 (SAR)。强效 DOT1L 抑制剂对 MLL 易位白血病细胞系 MV4;11 和 THP1 的增殖具有选择性活性，EC 504–11 μM 的值。等温滴定量热研究表明，两种代表性抑制剂以高亲和力与 DOT1L:核小体复合物结合，仅与酶辅因子 SAM（S-腺苷-1-甲硫氨酸）竞争，而不与底物核小体竞争。
• Design, synthesis and biological evaluation of novel aminopropylcarboxamide derivatives as sigma ligands
  作者：Daniele Zampieri、Sara Fortuna、Maurizio Romano、Emanuele Amata、Maria Dichiara、Agostino Marrazzo、Lorella Pasquinucci、Rita Turnaturi、Maria Grazia Mamolo

  DOI：10.1016/j.bmcl.2022.128860

  日期：2022.9

  novel sigma receptor (SR) ligands, we present the design, synthesis and binding studies of a small library of aminopropylcarboxamide derivatives, obtained from a deconstruction of the piperidine ring of previously synthesized piperidine-based compounds. The best results were achieved with benzofuran (5c, 5g) and quinoline (5a, 5e) derivatives. These compounds revealed the highest affinity for both receptor

  在我们不断努力开发新的 σ 受体 (SR) 配体的过程中，我们提出了一个小型氨基丙基甲酰胺衍生物库的设计、合成和结合研究，该库是从先前合成的基于哌啶的化合物的哌啶环的解构中获得的。苯并呋喃（5c，5g）和喹啉（5a，5e）衍生物的效果最好。这些化合物显示出对两种受体亚型的最高亲和力。特别是 3,4-二甲氧基苯基衍生物5e和5g对 S2R 表现出最高的选择性，尤其是喹啉衍生物5e对 S2R 亚型的亲和力高出 35 倍。针对广泛用于乳腺癌研究的 SKBR3 和 MCF7 细胞系评估了上述化合物的细胞毒活性。尽管5g的效力与西拉美新和氟哌啶醇在两种细胞系中的效力相似，但化合物5a、5c和5e在 SKBR3 细胞中表现出至少与氟哌啶醇相当的效力。对 S2R 结合位点的分子模型评估证实了化合物5e的强相互作用，从而证明了其最高的 S2R 亲和力。
• Substituted carboxylic acid derivatives
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP0512352A2

  公开（公告）日：1992-11-11

  The compounds of the formula wherein A, B, Q, Ri, R2, R2', X, Y, Z and n are as described in claim 1, when appropriate, in the form of enantiomers, racemates, diastereomeres or mixtures thereof or geometric isomers or mixtures thereof and, when a basic or acidic group is present, pharmaceutically acceptable salts thereof inhibit enzyme carnitine acyltransferase 1 (CAT-1) and are therefore useful in the prevention of injury to ischemic tissue, and can limit infarct size, improve cardiac function and prevent arrhythmias during and following a myocardial infarction. They can be prepared according to various methods which are known per se.

  式中的化合物 其中 A、B、Q、Ri、R2、R2'、X、Y、Z 和 n 如权利要求 1 所述，适当时以对映体、外消旋体、非对映异构体或其混合物或几何异构体或其混合物的形式存在，当存在碱性或酸性基团时、其药学上可接受的盐类可抑制肉碱酰基转移酶 1（CAT-1），因此可用于预防缺血组织损伤，并可在心肌梗塞期间和之后限制梗塞面积、改善心功能和预防心律失常。它们可以按照各种已知的方法制备。
• Design and synthesis of 4-benzylpiperidine carboxamides as dual serotonin and norepinephrine reuptake inhibitors
  作者：Suresh Paudel、Yongkai Cao、Shuohan Guo、Byeongkwan An、Kyeong-Man Kim、Seung Hoon Cheon

  DOI：10.1016/j.bmc.2015.08.022

  日期：2015.10

  A series of 4-benzylpiperidine carboxamides were designed and synthesized, and tested for their dual (serotonin and norepinephrine) reuptake inhibition. The synthesis of 4-benzylpiperidine carboxamides involved two main steps: amidation and substitution. Derivatives with 3 carbon linker displayed better activity than with 2 carbon linker. 4-Biphenyl- and 2-naphthyl-substituted derivatives 7e and 7j showed greater dual reuptake inhibition than standard drug venlafaxine HCl. (C) 2015 Elsevier Ltd. All rights reserved.
• US5344843A
  申请人：——

  公开号：US5344843A

  公开（公告）日：1994-09-06