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1-(1,3-thiazol-5-ylmethyl)piperazine | 1310212-29-3

中文名称
——
中文别名
——
英文名称
1-(1,3-thiazol-5-ylmethyl)piperazine
英文别名
5-(piperazin-1-ylmethyl)thiazole;1-[(1,3-Thiazol-5-yl)methyl]piperazine;5-(piperazin-1-ylmethyl)-1,3-thiazole
1-(1,3-thiazol-5-ylmethyl)piperazine化学式
CAS
1310212-29-3
化学式
C8H13N3S
mdl
——
分子量
183.277
InChiKey
OLFBTDYWKRJXSH-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

物化性质

  • 沸点:
    300.3±27.0 °C(Predicted)
  • 密度:
    1.185±0.06 g/cm3(Predicted)

计算性质

  • 辛醇/水分配系数(LogP):
    0.2
  • 重原子数:
    12
  • 可旋转键数:
    2
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.62
  • 拓扑面积:
    56.4
  • 氢给体数:
    1
  • 氢受体数:
    4

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    描述:
    1-(1,3-thiazol-5-ylmethyl)piperazine4-(1-哌嗪基)-1H-吲哚二氯甲烷 为溶剂, 反应 0.5h, 生成 N-phenyl-4-(thiazol-5-ylmethyl)piperazine-1-carboxamide
    参考文献:
    名称:
    Discovery and optimization of aspartate aminotransferase 1 inhibitors to target redox balance in pancreatic ductal adenocarcinoma
    摘要:
    Pancreatic ductal adenocarcinoma (PDAC) is a lethal malignancy that is extremely refractory to the therapeutic approaches that have been evaluated to date. Recently, it has been demonstrated that PDAC tumors are dependent upon a metabolic pathway involving aspartate aminotransferase 1, also known as glutamate-oxaloacetate transaminase 1 (GOT1), for the maintenance of redox homeostasis and sustained proliferation. As such, small molecule inhibitors targeting this metabolic pathway may provide a novel therapeutic approach for the treatment of this devastating disease. To this end, from a high throughput screen of similar to 800,000 molecules, 4-(1H-indol-4-yl)-N-phenylpiperazine-1-carboxamide was identified as an inhibitor of GOT1. Mouse pharmacokinetic studies revealed that potency, rather than inherent metabolic instability, would limit immediate cell- and rodent xenograft-based experiments aimed at validating this potential cancer metabolism-related target. Medicinal chemistry-based optimization resulted in the identification of multiple derivatives with >10-fold improvements in potency, as well as the identification of a tryptamine-based series of GOT1 inhibitors. (C) 2018 Elsevier Ltd. All rights reserved.
    DOI:
    10.1016/j.bmcl.2018.04.061
  • 作为产物:
    参考文献:
    名称:
    Enzyme Inhibitors
    摘要:
    式(I)的化合物是极光激酶抑制剂:其中X是—N—、—CH2—N—、—CH2—CH—或—CH—;R1是式(IA)的基团,其中Z是—CH2—、—NH—、-O-、—S(O)—、—S—、—S(O)2或具有3-7个环原子的二价单环碳环或杂环基团;Alk是任选取代的二价C1-C6亚烷基基团;A是氢或任选取代的具有5-7个环原子的单环碳环或杂环环;r、s和t独立地为0或1,前提是当A为氢时,至少一个r和s为1;R2是卤素、—CN、—CF3、—OCH3或环丙基;R3是式(IB)的基团,其中Q是氢或任选取代的苯基或具有5或6个环原子的单环杂环环;Z<1>是—S—、—S(O)—、—S(O)2—、—O—、—SO2NH—、—NHSO2—、NHC(═O)NH、—NH(C═S)NH—或—N(R4)—,其中R4是氢、C1-C3烷基、环烷基或苄基;Alk<1>和Alk<2>独立地是任选取代的二价C1-C3亚烷基基团;m、n和p独立地为0或1。数据来自esp@cenet数据库—Worldwide d77。
    公开号:
    US20090247507A1
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文献信息

  • ENZYME INHIBITORS
    申请人:The Institute of Cancer Research
    公开号:EP1963315A2
    公开(公告)日:2008-09-03
  • US8088761B2
    申请人:——
    公开号:US8088761B2
    公开(公告)日:2012-01-03
  • [EN] ENZYME INHIBITORS<br/>[FR] INHIBITEURS D'ENZYMES
    申请人:CHROMA THERAPEUTICS LTD
    公开号:WO2007072017A2
    公开(公告)日:2007-06-28
    [EN] Compounds of of formula (I), are aurora kinase inhibitors:wherein X is -N-, -CH2-N-, -CH2-CH-, or -CH-; R1 is a radical of formula (IA) wherein Z is -CH2-, -NH-, -0-, -S(O)- -S-, -S(O)2 or a divalent monocyclic carbocyclic or heterocyclic radical having 3-7 ring atoms; Alk is an optionally substituted divalent C1-C6 alkylene radical; A is hydrogen or an optionally substituted monocyclic carbocyclic or heterocyclic ring having 5-7 ring atoms; r, s and t are independently 0 or 1 , provided that when A is hydrogen then at least one of r and s is 1 ; R2 is halogen, -CN, -CF3, -OCH3, or cyclopropyl; and R3 is a radical of formula (IB) wherein Q is hydrogen or an optionally substituted phenyl or monocyclic heterocyclic ring with 5 or 6 ring atoms; Z1 is -S-, -S(O)-, -S(O)2-, -O-, -SO2NH-, -NHSO2-, NHC(=O)NH, -NH(C=S)NH-, Or -N(R4)- wherein R4 is hydrogen, C1-C3 alkyl, cycloalkyl, or benzyl; and Alk1 and Alk2 are, independently, optionally substituted divalent C1-C3 alkylene radicals; and m, n and p are independently 0 or 1.
    [FR] L'invention concerne des composés représentés par la formule générale (I). Ces composés sont des inhibiteurs d'Aurora kinases. Dans ladite formule, X désigne un groupe -N-, -CH2-N-, -CH2-CH-, ou -CH-°; R1 désigne un radical représenté par la formule générale (IA), dans laquelle Z désigne un groupe -CH2-, -NH-, -O-, -S(O)- -S-, -S(O)2 ou un radical hétérocyclique ou carbocyclique monocyclique divalent comportant 3-7 atomes par cycle°; Alk désigne un radical alkylène C1-C6 divalent éventuellement substitué ; A désigne un atome d'hydrogène ou un noyau hétérocyclique ou carbocyclique monocyclique éventuellement substitué comportant 5-7 atomes par cycle°; r, s et t valent chacun 0 ou 1, à condition que lorsque A désigne un atome d'hydrogène, alors r et/ou s vaut 1 ; R2 désigne un groupe halogène, -CN, -CF3, -OCH3, ou cyclopropyle°; et R3 désigne un radical représenté par la formule générale (IB), dans laquelle Q désigne un atome d'hydrogène ou un noyau hétérocyclique monocyclique ou phényle éventuellement substitué comportant 5-6 atomes par cycle ; Z1 désigne un groupe -S-, -S(O)-, -S(O)2-, -O-, -SO2NH-, -NHSO2-, NHC(=O)NH, -NH(C=S)NH-, ou -N(R4)-, R4 désignant un atome d'hydrogène, un groupe alkyle C1-C3, cycloalkyle, ou benzyle°; et Alk1 et Alk2 désignent, chacun des radicaux alkylène C1-C3 divalents éventuellement substitués ; et m, n et p valent chacun 0 ou 1.
  • Discovery and optimization of aspartate aminotransferase 1 inhibitors to target redox balance in pancreatic ductal adenocarcinoma
    作者:Justin Anglin、Reza Beheshti Zavareh、Philipp N. Sander、Daniel Haldar、Edouard Mullarky、Lewis C. Cantley、Alec C. Kimmelman、Costas A. Lyssiotis、Luke L. Lairson
    DOI:10.1016/j.bmcl.2018.04.061
    日期:2018.9
    Pancreatic ductal adenocarcinoma (PDAC) is a lethal malignancy that is extremely refractory to the therapeutic approaches that have been evaluated to date. Recently, it has been demonstrated that PDAC tumors are dependent upon a metabolic pathway involving aspartate aminotransferase 1, also known as glutamate-oxaloacetate transaminase 1 (GOT1), for the maintenance of redox homeostasis and sustained proliferation. As such, small molecule inhibitors targeting this metabolic pathway may provide a novel therapeutic approach for the treatment of this devastating disease. To this end, from a high throughput screen of similar to 800,000 molecules, 4-(1H-indol-4-yl)-N-phenylpiperazine-1-carboxamide was identified as an inhibitor of GOT1. Mouse pharmacokinetic studies revealed that potency, rather than inherent metabolic instability, would limit immediate cell- and rodent xenograft-based experiments aimed at validating this potential cancer metabolism-related target. Medicinal chemistry-based optimization resulted in the identification of multiple derivatives with >10-fold improvements in potency, as well as the identification of a tryptamine-based series of GOT1 inhibitors. (C) 2018 Elsevier Ltd. All rights reserved.
  • Enzyme Inhibitors
    申请人:Bavetsias Vassilios
    公开号:US20090247507A1
    公开(公告)日:2009-10-01
    Compounds of formula (I), are aurora kinase inhibitors: wherein X is —N—, —CH2—N—, —CH2—CH—, or —CH—; R1 is a radical of formula (IA) wherein Z is —CH2—, —NH—, -0-, —S(O)— —S—, —S(O)2 or a divalent monocyclic carbocyclic or heterocyclic radical having 3-7 ring atoms; Alk is an optionally substituted divalent C1-C6 alkylene radical; A is hydrogen or an optionally substituted monocyclic carbocyclic or heterocyclic ring having 5-7 ring atoms; r, s and t are independently 0 or 1, provided that when A is hydrogen then at least one of r and s is 1; R2 is halogen, —CN, —CF3, —OCH3, or cyclopropyl; and R3 is a radical of formula (IB) wherein Q is hydrogen or an optionally substituted phenyl or monocyclic heterocyclic ring with 5 or 6 ring atoms; Z&It;1> is —S—, —S(O)—, —S(O)2—, —O—, —SO2NH—, —NHSO2—, NHC(═O)NH, —NH(C═S)NH—, Or —N(R4)—wherein R4 is hydrogen, C1-C3 alkyl, cycloalkyl, or benzyl; and Alk&It;1> and Alk&It;2> are, independently, optionally substituted divalent C1-C3 alkylene radicals; and m, n and p are independently 0 or 1. Data supplied from the esp@cenet datatbase—Worldwide d77
    式(I)的化合物是极光激酶抑制剂:其中X是—N—、—CH2—N—、—CH2—CH—或—CH—;R1是式(IA)的基团,其中Z是—CH2—、—NH—、-O-、—S(O)—、—S—、—S(O)2或具有3-7个环原子的二价单环碳环或杂环基团;Alk是任选取代的二价C1-C6亚烷基基团;A是氢或任选取代的具有5-7个环原子的单环碳环或杂环环;r、s和t独立地为0或1,前提是当A为氢时,至少一个r和s为1;R2是卤素、—CN、—CF3、—OCH3或环丙基;R3是式(IB)的基团,其中Q是氢或任选取代的苯基或具有5或6个环原子的单环杂环环;Z<1>是—S—、—S(O)—、—S(O)2—、—O—、—SO2NH—、—NHSO2—、NHC(═O)NH、—NH(C═S)NH—或—N(R4)—,其中R4是氢、C1-C3烷基、环烷基或苄基;Alk<1>和Alk<2>独立地是任选取代的二价C1-C3亚烷基基团;m、n和p独立地为0或1。数据来自esp@cenet数据库—Worldwide d77。
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同类化合物

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