1-Methyl-4-(2-piperazin-1-yl-ethyl)-piperazine | 1018603-40-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 1-Methyl-4-(2-piperazin-1-yl-ethyl)-piperazine
• 英文别名: 1-methyl-4-(2-piperazin-1-ylethyl)piperazine
• CAS: 1018603-40-1
• 化学式: C₁₁H₂₄N₄
• 分子量: 212.338
• InChiKey: OLEPFFNHBIVUAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  21.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-amino-1-iodo-4,5-dimethoxyanthracene-9,10-dione 、 1-Methyl-4-(2-piperazin-1-yl-ethyl)-piperazine 在 三溴化硼 、 三氟甲烷磺酸亚铜(I)苯联合体 (2:1) 、 potassium carbonate 作用下， 以 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 5,7-dihydroxy-2-(4-(2-(4-methylpiperazin-1-yl)ethyl)piperazin-1-yl)anthra[2,1-d]thiazole-6,11-dione
  参考文献：
  名称：

  基于天然产物的设计，合成和生物评价大黄中作为新型抗肿瘤药的蒽[2,1 - d ]噻唑-6,11-二酮衍生物

  摘要：

  设计，合成了两类新型的天然大黄酸2-取代的5,7-二羟基蒽[2,1- d ]噻唑-6,11-二酮衍生物，对人癌细胞A549和HeLa的体外抗肿瘤活性。

  DOI：

  10.1016/j.ejmech.2014.07.047
• 作为产物：
  描述：

  叔丁基-4-(2-羟乙基)哌嗪-1-羧酸酯 在 4-二甲氨基吡啶 、 甲基磺酰氯 、 三乙胺 、 三氟乙酸 、 sodium iodide 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 1-Methyl-4-(2-piperazin-1-yl-ethyl)-piperazine
  参考文献：
  名称：

  基于天然产物的设计，合成和生物评价大黄中作为新型抗肿瘤药的蒽[2,1 - d ]噻唑-6,11-二酮衍生物

  摘要：

  设计，合成了两类新型的天然大黄酸2-取代的5,7-二羟基蒽[2,1- d ]噻唑-6,11-二酮衍生物，对人癌细胞A549和HeLa的体外抗肿瘤活性。

  DOI：

  10.1016/j.ejmech.2014.07.047

文献信息

• SUBSTITUTED PYRIDINYL-PYRIMIDINES AND THEIR USE AS MEDICAMENTS
  申请人：Dahmann Georg

  公开号：US20130023502A1

  公开（公告）日：2013-01-24

  The invention relates to new substituted pyridinyl-pyrimidines of formula 1 wherein ring A is a five-membered saturated or unsaturated carbocyclic ring which optionally comprises one, two or three heteroatoms each independently from each other selected from the group N, S and O, wherein R 1 , R 2 , R 4 , R 3 , R 5 and R 6 are defined as in claim 1 and wherein ring A is further optionally substituted by one or two further substituents and the pharmaceutically acceptable salts, diastereomers, enantiomers, racemates, hydrates and solvates of the aforementioned compounds.

  该发明涉及公式1中的新取代吡啶基嘧啶化合物， 其中环A是一个含有五个成员的饱和或不饱和碳环，该环可选地包含一个、两个或三个异原子，每个异原子独立地选自N、S和O组成， 其中R1、R2、R4、R3、R5和R6如权利要求书中所定义，并且环A进一步可选地被一个或两个进一步取代基取代，以及上述化合物的药用盐、二对映体、对映体、消旋体、水合物和溶剂化合物。
• [EN] SUBSTITUTED PYRIDINYL-PYRIMIDINES AND THEIR USE AS MEDICAMENTS<br/>[FR] PYRIDINYL-PYRIMIDINES SUBSTITUÉES ET LEUR UTILISATION EN TANT QUE MÉDICAMENTS
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2012101013A1

  公开（公告）日：2012-08-02

  The invention relates to new substituted pyridinyl-pyrimidines of formula 1 wherein ring A is a five-membered saturated or unsaturated carbocyclic ring which optionally comprises one, two or three heteroatoms each independently from each other selected from the group N, S and O, wherein R1, R2, R4, R3, R5 and R6 are defined as in claim 1 and wherein ring A is further optionally substituted by one or two further substituents and the pharmaceutically acceptable salts, diastereomers, enantiomers, racemates, hydrates and solvates of the aforementioned compounds.

  该发明涉及公式1中的新取代吡啶基嘧啶，其中环A是一个五元饱和或不饱和碳环，可选地包含一个、两个或三个异原子，每个异原子独立地选自N、S和O组，其中R1、R2、R4、R3、R5和R6如权利要求1中所定义，环A进一步可选地被一个或两个进一步取代基取代，以及上述化合物的药学上可接受的盐、二对映体、对映体、消旋体、水合物和溶剂化合物。
• Treatment of skin lesions
  申请人：PIQUR THERAPEUTICS AG

  公开号：US10993947B2

  公开（公告）日：2021-05-04

  The present invention is relates to a compound of formula (I), wherein X1, X2 and X3 are, independently of each other, N or CH; with the proviso that at least two of X1, X2 and X3 are N; Y is N or CH; W is H or F; with the proviso that when W is F, then X1, X2 and X3 are N; R1 and R2 are independently of each other (i) a morpholinyl of formula (II) wherein the arrow denotes the bond in formula (I); and wherein R3 and R4 are independently of each other H, C1-C3alkyl optionally substituted with one or two OH, C1-C2fluoroalkyl, C1-C2alkoxy, C1-C2alkoxyC1-C3alkyl, CN, or C(O)O—C1-C2alkyl; or R3 and R4 form together a bivalent residue —R5R6— selected from C1-C3alkylene optionally substituted with 1 to 4 F, —CH2—O—CH2—, —CH2—NH—CH2—, or any of the structures wherein the arrows denote the bonds in formula (II); or (ii) a saturated 6-membered heterocyclic ring Z selected from thiomorpholinyl and piperazinyl, optionally substituted by 1 to 3 R7; wherein R7 is independently at each occurrence C1-C3alkyl optionally substituted with one or two OH, C1-C2fluoroalkyl, C1-C2alkoxyC1-C3alkyl, C3-C6cycloalkyl; or two R7 substituents form together a bivalent residue —R8R9— selected from C1-C3alkylene optionally substituted with 1 to 4 F, —CH2—O—CH2— or —O—CH2CH2—O—; with the proviso that at least one of R1 and R2 is a morpholinyl of formula II; and prodrugs, metabolites, tautomers, solvates and pharmaceutically acceptable salts thereof, for use in the prevention or treatment of a skin lesion in a subject.

  本发明涉及一种式 (I) 的化合物、 其中 X1、X2 和 X3 相互独立地是 N 或 CH；但条件是 X1、X2 和 X3 中至少有两个是 N； Y 是 N 或 CH W 是 H 或 F；但当 W 是 F 时，X1、X2 和 X3 是 N； R1 和 R2 相互独立 (i) 式（II）的吗啉基 其中箭头表示式（I）中的键；以及 其中 R3 和 R4 相互独立地为 H、任选被一个或两个 OH、C1-C2-氟烷基、C1-C2-烷氧基、C1-C2-烷氧基 C1-C3烷基、CN 或 C(O)O-C1-C2烷基取代的 C1-C3 烷基；或 R3 和 R4 共同形成选自任选被 1 至 4 个 F、-CH2-O-CH2-、-CH2-NH-CH2-或任何结构取代的 C1-C3 烷烯的二价残基-R5R6-。 其中箭头表示式（II）中的键；或 (ii) 选自硫代吗啉基和哌嗪基的饱和 6 元杂环 Z，任选被 1 至 3 个 R7 取代；其中 R7 在每次出现时均独立地为任选被一个或两个 OH、C1-C2 氟烷基、C1-C2 烷氧基 C1-C3 烷基、C3-C6 环烷基取代的 C1-C3 烷基；或两个 R7 取代基共同形成二价残基-R8R9-，该残基选自任选被 1 至 4 个 F、-CH2-O-CH2-或 -O-CH2CH2-O-取代的 C1-C3 烷基； 但 R1 和 R2 中至少有一个是式 II 的吗啉基； 及其原药、代谢物、同系物、溶剂和药学上可接受的盐，用于预防或治疗受试者的皮肤损伤。
• TREATMENT OF SKIN LESIONS
  申请人：PIQUR THERAPEUTICS AG

  公开号：US20190290653A1

  公开（公告）日：2019-09-26

  The present invention is relates to a compound of formula (I), wherein X 1 , X 2 and X 3 are, independently of each other, N or CH; with the proviso that at least two of X 1 , X 2 and X 3 are N; Y is N or CH; W is H or F; with the proviso that when W is F, then X 1 , X 2 and X 3 are N; R 1 and R 2 are independently of each other (i) a morpholinyl of formula (II) wherein the arrow denotes the bond in formula (I); and wherein R 3 and R 4 are independently of each other H, C 1 -C 3 alkyl optionally substituted with one or two OH, C 1 -C 2 fluoroalkyl, C 1 -C 2 alkoxy, C 1 -C 2 alkoxyC 1 -C 3 alkyl, CN, or C(O)O—C 1 -C 2 alkyl; or R 3 and R 4 form together a bivalent residue —R 5 R 6 — selected from C 1 -C 3 alkylene optionally substituted with 1 to 4 F, —CH 2 —O—CH 2 —, —CH 2 —NH—CH 2 —, or any of the structures wherein the arrows denote the bonds in formula (II); or (ii) a saturated 6-membered heterocyclic ring Z selected from thiomorpholinyl and piperazinyl, optionally substituted by 1 to 3 R 7 ; wherein R 7 is independently at each occurrence C 1 -C 3 alkyl optionally substituted with one or two OH, C 1 -C 2 fluoroalkyl, C 1 -C 2 alkoxyC 1 -C 3 alkyl, C 3 -C 6 cycloalkyl; or two R 7 substituents form together a bivalent residue —R 8 R 9 — selected from C 1 -C 3 alkylene optionally substituted with 1 to 4 F, —CH 2 —O—CH 2 — or —O—CH 2 CH 2 —O—; with the proviso that at least one of R 1 and R 2 is a morpholinyl of formula II; and prodrugs, metabolites, tautomers, solvates and pharmaceutically acceptable salts thereof, for use in the prevention or treatment of a skin lesion in a subject.
• TREATMENT OF SKIN DISORDERS
  申请人：PIQUR THERAPEUTICS AG

  公开号：US20210107913A1

  公开（公告）日：2021-04-15

  The present invention relates to a compound of formula (I), wherein X 1 , X 2 and X 3 are, independently of each other, N or CH; with the proviso that at least two of X 1 X 2 and X 3 are N; Y is N or CH; W is H or F; with the proviso that when W is F, then Xi, X 2 and X 3 are N; R 1 and R 2 are independently of each other (i) a morpholinyl of formula (II) wherein the arrow denotes the bond in formula (I); and wherein R 3 and R 4 are independently of each other H, C 1 -C 3 alkyl optionally substituted with one or two OH, C 1 -C 2 fluoroalkyl, C 1 -C 2 alkoxy, C 1 -C 2 alkoxyC 1 -C 3 alkyl, CN, or C(O)O—C 1 -C 2 alkyl; or R 3 and R 4 form together a bivalent residue —R 5 R 6 — selected from C 1 -C 3 alkylene optionally substituted with 1 to 4 F, —CH 2 —O—CH 2 —, —CH 2 —NH—CH 2 —, or any of the structures wherein the arrows denote the bonds in formula (II); or (ii) a saturated 6-membered heterocyclic ring Z selected from thiomorpholinyl and piperazinyl, optionally substituted by 1 to 3 R 7 ; wherein R 7 is independently at each occurrence C 1 -C 3 alkyl optionally substituted with one or two OH, C 1 -C 2 fluoroalkyl, C 1 -C 2 alkoxyC 1 -C 3 alkyl, C 3 -C 6 cycloalkyl; or two R 7 substituents form together a bivalent residue —R 8 R 9 — selected from C 1 -C 3 alkylene optionally substituted with 1 to 4 F, —CH 2 —O—CH 2 — or —O—CH 2 CH 2 —O—; with the proviso that at least one of R 1 and R 2 is a morpholinyl of formula II; and prodrugs, metabolites, tautomers, solvates and pharmaceutically acceptable salts thereof, for use in a method of treating a skin disorder in a subject, wherein said skin disorder is a genodermatosis, a vascular anomaly or a skin disorder selected from scleroderma, sclerodermatous chronic graft-versus-host disease, lichen sclerosus, lichen planus, lichen ruber planus and scars.