4-(1-piperazinyl)isoquinoline | 217816-47-2

• 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: 4-(1-piperazinyl)isoquinoline
• 英文别名: 4-Piperazin-1-ylisoquinoline；4-piperazin-1-yl-isoquinoline
• CAS: 217816-47-2
• 化学式: C₁₃H₁₅N₃
• 分子量: 213.282
• InChiKey: NIBZKHUIJGTBOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  28.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(2-chloroethyl)-7-methyl-5,6,7,8-tetrahydropyrido[4', 3':4,5]thieno[2,3-d]pyrimidin-4(3H)-one 、 4-(1-piperazinyl)isoquinoline 在 N,N-二异丙基乙胺 、 sodium bromide 作用下， 以 N-甲基吡咯烷酮 为溶剂， 生成 3-[2-(4-Isoquinolin-4-yl-piperazin-1-yl)-ethyl]-7-methyl-5,6,7,8-tetrahydro-3H-pyrido[4',3':4,5]thieno[2,3-d]pyrimidin-4-one
  参考文献：
  名称：

  Synthesis and SAR of highly potent dual 5-HT1A and 5-HT1B antagonists as potential antidepressant drugs

  摘要：

  Novel 5-HT1 autoreceptor ligands based on the N-4-aryl-piperazinyl-N'-ethyl-5,6,7,8-tetrahydropyrido[4', 3':4,5]thieno[2,3-d]pyrimidin-4(3H)-one core are described. Aiming at antidepressants with a novel mode of action our objective was to identify potent antagonists showing balanced affinities and high selectivity for the 5-HT1A and 5-HT1B receptors. Strategies for the development of dual 5-HT1A and 5-HT1B antagonists based on 1 and 2 as leads and the corresponding results are discussed. Isoquinoline analogue 33 displayed high affinity and an antagonistic mode of action for the 5-HT1A and the 5-HT1B receptors and was characterized further with respect to selectivity, electrically stimulated [H-3]5-HT release and in vivo efficacy. (c) 2005 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2005.04.077
• 作为产物：
  描述：

  tert-butyl 4-(isoquinolin-4-yl)piperazine-1-carboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以67%的产率得到4-(1-piperazinyl)isoquinoline
  参考文献：
  名称：

  2-substituted 1,2-benzisothiazole derivatives and their use as serotonin antagonists (5-HT1A, 5HT1B and 5-HT1D)

  摘要：

  在这里，取代基具有描述中指示的含义，它们的制备和用途作为5-羟色胺拮抗剂。

  公开号：

  US06346622B1

文献信息

• N-arylheteroaromatic products compositions containing them and use thereof
  申请人：Le-Brun Alain

  公开号：US20050130989A1

  公开（公告）日：2005-06-16

  N-Arylheteroaromatic products, compositions containing them and use thereof. The present invention relates to novel chemical compounds, particularly to novel N-arylheteroaromatic products, to compositions containing them and to their use as medicinal products, in particular in oncology.

  N-芳基杂芳产物，含有它们的组合物及其用途。本发明涉及新型化合物，特别是新型N-芳基杂芳产物，含有它们的组合物以及它们作为药用产品的用途，特别是在肿瘤学中的用途。
• New .MU.-Opioid Receptor Agonists with Piperazine Moiety.
  作者：Teruo KOMOTO、Tomomi OKADA、Susumu SATO、Yasuhiro NIINO、Tetsuo OKA、Takao SAKAMOTO

  DOI：10.1248/cpb.49.1314

  日期：——

  New μ-opioid receptor (MOR) agonists containing piperazine and homopiperazine moieties in the structures were synthesized and their affinities to and agonist potencies on MOR were evaluated. Among the synthesized compounds, 4-[4-(2-methoxyphenyl)piperazin-1-yl]-N,N-dimethyl-2,2-diphenylbutanamide (20Aa) showed the highest affinity to the human MOR expressed in Chinese hamster ovary (CHO)-K1 cells, and the highest agonist potency on the MOR in isolated guinea-pig ileum preparation.

  新μ-阿片受体（MOR）激动剂的合成及其对MOR的亲和力和激动效力研究。含哌嗪和同哌嗪结构的新型μ-阿片受体（MOR）激动剂被合成，并评估了它们对MOR的亲和力和激动效力。在合成的化合物中，4-[4-(2-甲氧基苯基)哌嗪-1-基]-N,N-二甲基-2,2-二苯基丁酰胺（20Aa）显示出对在中华仓鼠卵巢（CHO）-K1细胞中表达的人类MOR的最高亲和力，并且在离体豚鼠回肠制备中对MOR具有最高的激动效力。
• Utilization of pyrimidine derivatives for preventing and treating cerebral ischaemia
  申请人：BASF Aktiengesellschaft

  公开号：US06387912B1

  公开（公告）日：2002-05-14

  Use of pyrimidine derivatives of the formula I where the substituents are as defined in the description, and of their physiologically tolerated salts for producing medicaments for the prophylaxis and treatment of cerebral ischemia and strokes.

  使用公式I中定义的取代基的嘧啶衍生物，以及它们的生理耐受盐用于生产用于预防和治疗脑缺血和中风的药物。
• 3-substituted pyrido [3',4':4,5] Thieno [2,3-d] pyrimidine derivatives,
  申请人：BASF Aktiengesellschaft

  公开号：US06159981A1

  公开（公告）日：2000-12-12

  3-Substituted 3,4,5,6,7,8-hexahydropyrido [3',4':4,5]-thieno[2,3-d]pyrimidine derivatives of the formula I ##STR1## where R.sup.1 is a hydrogen atom, a C.sub.1 -C.sub.4 -alkyl group, an acetyl group, a phenylalkyl C.sub.1 -C.sub.4 radical, the aromatic system being unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 -alkyl, trifluoromethyl, hydroxyl, C.sub.1 -C.sub.4 -alkoxy, amino, cyano or nitro groups, or is a phenylalkanone radical, it being possible for the phenyl group to be substituted by halogen, R.sup.2 is a phenyl, pyridyl, pyrimidinyl or pyrazinyl group which is unsubstituted or mono- or disubstituted by halogen atoms, C.sub.1 -C.sub.4 -alkyl, trifluoromethyl, trifluoromethoxy, hydroxyl, C.sub.1 -C.sub.4 -alkoxy, amino, monomethylamino, dimethylamino, cyano or nitro groups and which may be fused to a benzene nucleus which can be unsubstituted or mono- or disubstituted by halogen atoms, C.sub.1 -C.sub.4 -alkyl, hydroxyl, trifluoromethyl, C.sub.1 -C.sub.4 -alkoxy, amino, cyano or nitro groups and may contain 1 nitrogen atom, or to a 5- or 6-membered ring which may contain 1-2 oxygen atoms, A is NH or an oxygen atom, Y is CH.sub.2, CH.sub.2 --CH.sub.2, CH.sub.2 --CH.sub.2 --CH.sub.2 or CH.sub.2 --CH, Z is a nitrogen atom, carbon atom or CH, it also being possible for the linkage between Y and Z to be a double bond, and n is 2, 3 or 4, and the physiologically tolerated salts thereof.

  3-取代的3,4,5,6,7,8-六氢吡啶[3',4':4,5]-噻吩[2,3-d]嘧啶衍生物的结构式为I ##STR1## 其中R.sup.1是氢原子，C.sub.1-C.sub.4-烷基，乙酰基，苯基C.sub.1-C.sub.4基团，芳香环未取代或由卤素，C.sub.1-C.sub.4-烷基，三氟甲基，羟基，C.sub.1-C.sub.4-烷氧基，氨基，氰基或硝基取代，或是苯基酮基团，苯基可能被卤素取代；R.sup.2是未取代或单取代或双取代的苯基，吡啶基，嘧啶基或吡嗪基团，取代基为卤素原子，C.sub.1-C.sub.4-烷基，三氟甲基，三氟甲氧基，羟基，C.sub.1-C.sub.4-烷氧基，氨基，单甲基氨基，二甲基氨基，氰基或硝基，可能与苯环融合，苯环未取代或单取代或双取代，可能含有1个氮原子，或融合到含有1-2个氧原子的5-或6-成员环中；A为NH或氧原子，Y为CH.sub.2，CH.sub.2--CH.sub.2，CH.sub.2--CH.sub.2--CH.sub.2或CH.sub.2--CH，Z为氮原子，碳原子或CH，Y和Z之间的连接也可能是双键，n为2、3或4，并且其生理耐受的盐。
• [EN] N-ARYL HETEROAROMATIC PRODUCTS, COMPOSITIONS CONTAINING SAME AND USE THEREOF<br/>[FR] PRODUITS N-ARYL-HETEROAROMATIQUES, COMPOSITIONS LES CONTENANT ET UTILISATION
  申请人：AVENTIS PHARMA SA

  公开号：WO2004078732A1

  公开（公告）日：2004-09-16

  Produits N-aryl-hétéroaromatiques, compositions les contenant et utilisation. La présente invention concerne de nouveaux composés chimiques, particulièrement de nouveaux produits N-aryl-hétéroaromatiques, des compositions les contenant, et leur utilisation comme médicaments, en particulier en oncologie.

  这段文字的意思是：该发明涉及新的化合物，特别是新的N-芳基杂环芳香化合物、包含它们的组合物以及它们作为药物的用途，尤其是在肿瘤学中的应用。