N-[1-[(2-氯-5-噻唑基)甲基]-4-哌啶基]氨基甲酸叔丁酯 | 939986-54-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: N-[1-[(2-氯-5-噻唑基)甲基]-4-哌啶基]氨基甲酸叔丁酯
• 英文名称: tert-butyl N-{1-[(2-chlorothiazol-5-yl)methyl]piperidin-4-yl}carbamate
• 英文别名: tert-butyl 1-((2-chlorothiazol-5-yl)methyl)piperidin-4-ylcarbamate；[1-(2-Chloro-thiazol-5-ylmethyl)-piperidin-4-yl]-carbamic acid tert-butyl ester；tert-butyl N-[1-[(2-chloro-1,3-thiazol-5-yl)methyl]piperidin-4-yl]carbamate
• CAS: 939986-54-6
• 化学式: C₁₄H₂₂ClN₃O₂S
• 分子量: 331.867
• InChiKey: YXZZBHAUQUREIP-UHFFFAOYSA-N

物化性质

• 密度：
  1.25

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  82.7
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2934100090

反应信息

• 作为反应物：
  描述：

  N-[1-[(2-氯-5-噻唑基)甲基]-4-哌啶基]氨基甲酸叔丁酯 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 N-{1-[(2-chlorothiazol-5-yl)methyl]piperidin-4-yl}amine
  参考文献：
  名称：

  Design and synthesis of piperidine derivatives as novel human heat shock protein 70 inhibitors for the treatment of drug-resistant tumors

  摘要：

  HSP70 is a potential target for tumour treatment. HSP70 plays significant roles in several biological processes, including the regulation of apoptosis. In this study, piperidine derivatives were designed as novel HSP70 inhibitors based on virtual fragment screening performed in Dock 4.0, Discovery Studio 2.5 and SYBYL 6.9. A total of 67 novel piperidine derivatives were synthesized. Cell viability assays were performed in 16 cancer cell lines. The emphasis was placed on lapatinib-resistant breast cancer cells (BT/LapR1.0, MDA-MB-361, SK/Lap(R)1.0, and MDA-MB-453). The compounds HSP70-36/37/40/43146 significantly inhibited the proliferation of human breast cancer cells. Compound HSP70-36 inhibited the growth of BT474 and BT/Lap(R)1.0 cells with IC50 values of 1.41 mu M and 1.47 mu M, respectively. The binding affinity of HSP70-36/HSP70 was evaluated by surface plasmon resonance and yielded K-d values of 2.46 mu M. The LD50 was 869.0 mgkg(-1). These data suggest that HSP70-36 may be a potential candidate compound for tumour treatment. (C) 2015 The Authors. Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2015.04.043
• 作为产物：
  描述：

  2-氯-5-氯甲基噻唑 、 4-叔丁氧羰基氨基哌啶 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以98%的产率得到N-[1-[(2-氯-5-噻唑基)甲基]-4-哌啶基]氨基甲酸叔丁酯
  参考文献：
  名称：

  Design and synthesis of piperidine derivatives as novel human heat shock protein 70 inhibitors for the treatment of drug-resistant tumors

  摘要：

  HSP70 is a potential target for tumour treatment. HSP70 plays significant roles in several biological processes, including the regulation of apoptosis. In this study, piperidine derivatives were designed as novel HSP70 inhibitors based on virtual fragment screening performed in Dock 4.0, Discovery Studio 2.5 and SYBYL 6.9. A total of 67 novel piperidine derivatives were synthesized. Cell viability assays were performed in 16 cancer cell lines. The emphasis was placed on lapatinib-resistant breast cancer cells (BT/LapR1.0, MDA-MB-361, SK/Lap(R)1.0, and MDA-MB-453). The compounds HSP70-36/37/40/43146 significantly inhibited the proliferation of human breast cancer cells. Compound HSP70-36 inhibited the growth of BT474 and BT/Lap(R)1.0 cells with IC50 values of 1.41 mu M and 1.47 mu M, respectively. The binding affinity of HSP70-36/HSP70 was evaluated by surface plasmon resonance and yielded K-d values of 2.46 mu M. The LD50 was 869.0 mgkg(-1). These data suggest that HSP70-36 may be a potential candidate compound for tumour treatment. (C) 2015 The Authors. Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2015.04.043

文献信息

• N,N′ substituted piperidinamine compounds, and preparation method and usage thereof
  申请人：Institute of Pharmacology and Toxicology Academy of Military Medical Sciences P.L.A. China

  公开号：US10023565B2

  公开（公告）日：2018-07-17

  The present invention relates to a compound of formula (I), a stereomeride, pharmaceutically acceptable salt, a solvate or an N-oxide thereof, a medicine composition comprising the compound, a method for preparing the compound, and a usage of the compound in treating diseases related to Hsp70. The diseases are preferably selected from tumors, neurodegenerative diseases, and allogeneic transplantation rejection and infection.

  本发明涉及一种式(I)化合物、其立体异构体、药学上可接受的盐、溶液剂或N-氧化物，一种包含该化合物的药物组合物，一种制备该化合物的方法，以及该化合物在治疗与Hsp70有关的疾病中的用途。这些疾病优选选自肿瘤、神经退行性疾病、异体移植排斥和感染。
• [EN] N, N' SUBSTITUTED PIPERIDINAMINE COMPOUNDS, AND PREPARATION METHOD AND USAGE THEREOF<br/>[FR] COMPOSÉS N,N'-SUBSTITUÉS DE PIPÉRIDINAMINE, LEURS PROCÉDÉS DE PRÉPARATION ET UTILISATION CORRESPONDANTE<br/>[ZH] N，N'取代哌啶胺类化合物、其制备方法及用途
  申请人：INST PHARM & TOXICOLOGY AMMS

  公开号：WO2015090226A1

  公开（公告）日：2015-06-25

  本发明涉及式（I）的化合物、其立体异构体、可药用盐、溶剂化物或N-氧化物，包含所述化合物的药物组合物，所述化合物的制备方法，以及所述化合物用于治疗与Hsp70有关的疾病中的用途，其中所述疾病优选选自肿瘤、神经退行性疾病、异源移植的排斥和感染。
• N, N' SUBSTITUTED PIPERIDINAMINE COMPOUNDS, AND PREPARATION METHOD AND USAGE THEREOF
  申请人：Institute of Pharmacology and Toxicology Academy of Military Medical Sciences P.L.A. China

  公开号：EP3085701B1

  公开（公告）日：2019-02-20
• Design and synthesis of piperidine derivatives as novel human heat shock protein 70 inhibitors for the treatment of drug-resistant tumors
  作者：Yanqun Zeng、Ruiyuan Cao、Tianhong Zhang、Song Li、Wu Zhong

  DOI：10.1016/j.ejmech.2015.04.043

  日期：2015.6

  HSP70 is a potential target for tumour treatment. HSP70 plays significant roles in several biological processes, including the regulation of apoptosis. In this study, piperidine derivatives were designed as novel HSP70 inhibitors based on virtual fragment screening performed in Dock 4.0, Discovery Studio 2.5 and SYBYL 6.9. A total of 67 novel piperidine derivatives were synthesized. Cell viability assays were performed in 16 cancer cell lines. The emphasis was placed on lapatinib-resistant breast cancer cells (BT/LapR1.0, MDA-MB-361, SK/Lap(R)1.0, and MDA-MB-453). The compounds HSP70-36/37/40/43146 significantly inhibited the proliferation of human breast cancer cells. Compound HSP70-36 inhibited the growth of BT474 and BT/Lap(R)1.0 cells with IC50 values of 1.41 mu M and 1.47 mu M, respectively. The binding affinity of HSP70-36/HSP70 was evaluated by surface plasmon resonance and yielded K-d values of 2.46 mu M. The LD50 was 869.0 mgkg(-1). These data suggest that HSP70-36 may be a potential candidate compound for tumour treatment. (C) 2015 The Authors. Published by Elsevier Masson SAS.