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1,2,3,4,6,7,12,12a-Octahydropyrazino<2',1':6,1>pyrido<3,4-b>indole | 55344-28-0

分子结构分类

有机化合物 - 有机杂环化合物 - 吲哚及其衍生物

中文名称

——

中文别名

——

英文名称

1,2,3,4,6,7,12,12a-Octahydropyrazino<2',1':6,1>pyrido<3,4-b>indole

英文别名

1,2,3,4,6,7,12,12a-octahydropyrazino<2',1':6,1>pyrido<3,4-b>indol；1,2,3,4,6,7,12,12a-Octahydropyrazino(2',1':6,1)pyrido(3,4-b)indole；3,6,17-triazatetracyclo[8.7.0.03,8.011,16]heptadeca-1(10),11,13,15-tetraene

1,2,3,4,6,7,12,12a-Octahydropyrazino<2',1':6,1>pyrido<3,4-b>indole化学式

CAS

55344-28-0

化学式

C₁₄H₁₇N₃

mdl

——

分子量

227.309

InChiKey

FLWHGQJRIYDGPK-UHFFFAOYSA-N

BEILSTEIN

——

EINECS

——

物化性质

熔点：

215-217 °C
沸点：

419.8±45.0 °C(Predicted)
密度：

1.26±0.1 g/cm3(Predicted)

计算性质

辛醇/水分配系数(LogP)：

0.5
重原子数：

17
可旋转键数：

0
环数：

4.0
sp3杂化的碳原子比例：

0.43
拓扑面积：

31.1
氢给体数：

2
氢受体数：

2

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
——	1-Oxo-1,2,3,4,6,7,12,12a-octahydro-pyrazino<2',1':6,1>pyrido<3,4-b>indol	55344-27-9	C₁₄H₁₅N₃O	241.293

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	2-β-Aminoethyl-1,2,3,4,6,7,12,12a-octahydropyrazino<2',1':6,1>pyrido<3,4-b>indole	91119-31-2	C₁₆H₂₂N₄	270.377
——	2-(2-(4-Pyridyl)ethyl)-1,2,3,4,6,7,12,12a-octahydropyrazino(2',1':6,1)pyrido(3,4-b)indole	55344-34-8	C₂₁H₂₄N₄	332.448
——	2-Cyanomethyl 1,2,3,4,6,7,12,12a-octahydropyrazino<2',1':6,1>pyrido<3,4-b>indol	91119-30-1	C₁₆H₁₈N₄	266.346
——	2-β-(benzoyl)aminoethyl-1,2,3,4,6,7,12,12a-octahydropyrazino<2',1':6,1>pyrido<3,4-b>indole	72593-21-6	C₂₃H₂₆N₄O	374.486
——	N-[2-(3,4,6,7,12,12a-Hexahydro-1H-pyrazino[1',2':1,6]pyrido[3,4-b]indol-2-yl)-ethyl]-4-methyl-benzamide	72593-18-1	C₂₄H₂₈N₄O	388.513
——	4-Pyridinecarboxamide, N-(2-(3,4,6,7,12,12a-hexahydropyrazino(1',2':1,6)pyrido(3,4-b)indol-2(1H)-yl)ethyl)-	75144-39-7	C₂₂H₂₅N₅O	375.473
——	Ethamidindole	72593-08-9	C₂₄H₂₇N₅O₂	417.511
——	2-β-(4'-Aminobenzoyl)aminoethyl-1,2,3,4,6,7,12,12a-octahydropyrazino<2',1':6,1>pyrido<3,4-b>indole	72593-33-0	C₂₃H₂₇N₅O	389.5
——	Pyrazino(1',2':1,6)pyrido(3,4-b)indole, 1,2,3,4,6,7,12,12a-octahydro-2-(3-(4-fluorophenoxy)propyl)-	77294-04-3	C₂₃H₂₆FN₃O	379.477
——	4-Fluoro-N-[2-(3,4,6,7,12,12a-hexahydro-1H-pyrazino[1',2':1,6]pyrido[3,4-b]indol-2-yl)-ethyl]-benzamide	72593-35-2	C₂₃H₂₅FN₄O	392.476
——	2-methyl-N-[2-(3,6,17-triazatetracyclo[8.7.0.03,8.011,16]heptadeca-1(10),11,13,15-tetraen-6-yl)ethyl]benzamide	72593-13-6	C₂₄H₂₈N₄O	388.513
——	Benzamide, 4-chloro-N-(2-(3,4,6,7,12,12a-hexahydropyrazino(1',2':1,6)pyrido(3,4-b)indol-2(1H)-yl)ethyl)-	72593-14-7	C₂₃H₂₅ClN₄O	408.931
——	2-β-(4-Nitrobenzyl)aminoethyl-1,2,3,4,6,7,12,12a-octahydropyrazino<2',1':6,1>pyrido<3,4>indole	91119-36-7	C₂₃H₂₇N₅O₂	405.5
比立哌隆	2-γ-(p-Fluorobenzoylpropyl)-1,2,3,4,6,7,12,12a-octahydropyrazino<2',1':6,1>pyrido<3,4-b>indole	42021-34-1	C₂₄H₂₆FN₃O	391.488
——	2-β-(N-Phenylthioureido)-N'-ethyl-1,2,3,4,6,7,12,12a-octahydropyrazino<2',1':6,1>pyrido<3,4>indole	72593-32-9	C₂₃H₂₇N₅S	405.567
——	N-phenyl-3-(3,6,17-triazatetracyclo[8.7.0.03,8.011,16]heptadeca-1(10),11,13,15-tetraen-6-yl)propanamide	100222-02-4	C₂₃H₂₆N₄O	374.486
——	N-[2-(3,4,6,7,12,12a-Hexahydro-1H-pyrazino[1',2':1,6]pyrido[3,4-b]indol-2-yl)-ethyl]-4-methoxy-benzamide	72593-10-3	C₂₄H₂₈N₄O₂	404.512
——	2-β-(4-fluorobenzhydrylamino)ethyl-1,2,3,4,6,7,12,12a-octahydropyrazino<2',1':6,1>pyrido<3,4>indole	72593-38-5	C₂₉H₃₁FN₄	454.59
——	2-β-(4-Nitrobenzylideno)ethyl-1,2,3,4,6,7,12,12a-octahydropyrazino<2',1':6,1>pyrido<3,4>indole	91119-35-6	C₂₃H₂₅N₅O₂	403.484
——	6-[(E)-4-(4-fluorophenyl)pent-3-enyl]-3,6,17-triazatetracyclo[8.7.0.03,8.011,16]heptadeca-1(10),11,13,15-tetraene	——	C₂₅H₂₈FN₃	389.5
——	2-(3,3-Diphenyl-allyl)-1,2,3,4,6,7,12,12a-octahydro-pyrazino[1',2':1,6]pyrido[3,4-b]indole	77294-03-2	C₂₉H₂₉N₃	419.569
——	Chlorethindole	72593-09-0	C₂₃H₂₅ClN₄O	408.931
——	2-Amino-N-[2-(3,4,6,7,12,12a-hexahydro-1H-pyrazino[1',2':1,6]pyrido[3,4-b]indol-2-yl)-ethyl]-benzamide	72593-29-4	C₂₃H₂₇N₅O	389.5
二苯乙吲哚	2-β-(Benzhydryloxy)ethyl-1,2,3,4,6,7,12,12a-octahydropyrazino<2',1':6,1>pyrido<3,4-b>indole	72601-09-3	C₂₉H₃₁N₃O	437.585
——	Benzoic acid, 4-fluoro-2-(3,4,6,7,12,12a-hexahydropyrazino(1',2':1,6)pyrido(3,4-b)indol-2(1H)-yl)-, ethyl ester	77293-99-3	C₂₃H₂₄FN₃O₂	393.461
——	2-p-Chlorobenzoyl-1,2,3,4,6,7,12,12a-octahydropyrazino<2',1':6,1>pyrido<3,4-b>indole	77293-97-1	C₂₁H₂₀ClN₃O	365.862
——	2-β-(4'-Nitrobenzoyl)aminoethyl-1,2,3,4,6,7,12,12a-octahydropyrazino<2',1':6,1>pyrido<3,4-b>indole	75144-38-6	C₂₃H₂₅N₅O₃	419.483
N-(4-{[3-(3,4,6,7,12,12a-六氢吡喃联氮基[1',2':1,6]吡啶并[3,4-b]吲哚-2(1H)-基)丙基]硫烷基}苯基)乙酰胺	N-{4-[3-(3,4,6,7,12,12a-Hexahydro-1H-pyrazino[1',2':1,6]pyrido[3,4-b]indol-2-yl)-propylsulfanyl]-phenyl}-acetamide	115030-35-8	C₂₅H₃₀N₄OS	434.605
——	Pyrazino(1',2':1,6)pyrido(3,4-b)indole, 1,2,3,4,6,7,12,12a-octahydro-2-(4,4-bis(4-fluorophenyl)-3-butenyl)-	77294-02-1	C₃₀H₂₉F₂N₃	469.577
——	N-[2-(3,4,6,7,12,12a-Hexahydro-1H-pyrazino[1',2':1,6]pyrido[3,4-b]indol-2-yl)-ethyl]-4-methanesulfonyl-benzamide	72593-31-8	C₂₄H₂₈N₄O₃S	452.577
——	N-(2-Fluoro-phenyl)-3-(3,4,6,7,12,12a-hexahydro-1H-pyrazino[1',2':1,6]pyrido[3,4-b]indol-2-yl)-propionamide	100222-01-3	C₂₃H₂₅FN₄O	392.476
——	2-β-(4'-Fluorobenzhydryloxy)ethyl-1,2,3,4,6,7,12,12a-octahydropyrazino<2',1':6,1>pyrido<3,4-b>indole	72593-41-0	C₂₉H₃₀FN₃O	455.575
——	N-(2-Chloro-phenyl)-3-(3,4,6,7,12,12a-hexahydro-1H-pyrazino[1',2':1,6]pyrido[3,4-b]indol-2-yl)-propionamide	100222-00-2	C₂₃H₂₅ClN₄O	408.931
——	N-(2-ethylphenyl)-3-(3,6,17-triazatetracyclo[8.7.0.03,8.011,16]heptadeca-1(10),11,13,15-tetraen-6-yl)propanamide	100221-99-6	C₂₅H₃₀N₄O	402.539
——	2-methoxy-N-[2-(3,6,17-triazatetracyclo[8.7.0.03,8.011,16]heptadeca-1(10),11,13,15-tetraen-6-yl)ethyl]benzamide	72601-08-2	C₂₄H₂₈N₄O₂	404.512
——	2-{2-[(4-Chloro-phenyl)-(4-fluoro-phenyl)-methoxy]-ethyl}-1,2,3,4,6,7,12,12a-octahydro-pyrazino[1',2':1,6]pyrido[3,4-b]indole	91119-34-5	C₂₉H₂₉ClFN₃O	490.02
——	2-(δ-Phenyl-δ-p-fluorophenyl-δ-hydroxy)butyl-1,2,3,4,6,7,12,12a-octahydropyrazino<2',1':6,1>pyrido<3,4-b>indole	77294-00-9	C₃₀H₃₂FN₃O	469.602
——	3-(3,4,6,7,12,12a-Hexahydro-1H-pyrazino[1',2':1,6]pyrido[3,4-b]indol-2-yl)-N-(2-nitro-phenyl)-propionamide	100222-03-5	C₂₃H₂₅N₅O₃	419.483
——	N-[2-(3,4,6,7,12,12a-Hexahydro-1H-pyrazino[1',2':1,6]pyrido[3,4-b]indol-2-yl)-ethyl]-2-nitro-benzamide	72593-17-0	C₂₃H₂₅N₅O₃	419.483
——	2-γ-(p-Fluorobenzoyl)propyl-6-oxo-1,2,3,4,6,7,12,12a-octahydropyrazino<2',1':6,1>pyrido<3,4-b>indole	77294-07-6	C₂₄H₂₄FN₃O₂	405.472

反应信息

作为反应物：

描述：

1,2,3,4,6,7,12,12a-Octahydropyrazino<2',1':6,1>pyrido<3,4-b>indole 在 lithium aluminium tetrahydride 、 sodium carbonate 作用下，以四氢呋喃、 N,N-二甲基甲酰胺为溶剂，反应 37.0h，生成 2-β-(N-Phenylthioureido)-N'-ethyl-1,2,3,4,6,7,12,12a-octahydropyrazino<2',1':6,1>pyrido<3,4>indole

参考文献：

名称：

Saxena, Anil K.; Dhaon, Madhup K.; Ram, Siya, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1983, vol. 22, # 12, p. 1224 - 1232

摘要：

DOI：
作为产物：

描述：

1-Oxo-1,2,3,4,6,7,12,12a-octahydro-pyrazino<2',1':6,1>pyrido<3,4-b>indol 在 sodium tetrahydroborate 、三氟化硼乙醚作用下，以四氢呋喃为溶剂，反应 9.0h，以75%的产率得到1,2,3,4,6,7,12,12a-Octahydropyrazino<2',1':6,1>pyrido<3,4-b>indole

参考文献：

名称：

Sengupta, Sreela; Sahu, Devi P; Chatterjee, Sunil K, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1994, vol. 33, p. 285 - 287

摘要：

DOI：

点击查看最新优质反应信息

文献信息

Synthesis, biological evaluation, and quantitative structure-activity relationship analysis of [.beta.-(aroylamino)ethyl]piperazines and -piperidines and [2-[(arylamino)carbonyl]ethyl]piperazines, -piperidines, -pyrazinopyridoindoles, and -pyrazinoisoquinolines. A new class of potent H1 antagonists

作者：Mridula Saxena、Shiv K. Agarwal、G. K. Patnaik、Anil K. Saxena

DOI：10.1021/jm00173a011

日期：1990.11

Some [beta-(Aroylamino)ethyl]piperazines and -piperidines and [2-[(Arylamino)carbonyl]ethyl]piperazines, -piperidines, -pyrazinopyridoindoles, and -pyrazinoisoquinolines have been synthesized and their H1-antagonistic activity studied in isolated guinea pig ileum. Quantitative structure-activity relationship analysis indicates that the hydrophobicity of the side chain of these compounds plays a major

已经合成了一些[β-（芳酰基氨基）乙基]哌嗪和-哌啶和[2-[（芳基氨基羰基]乙基]哌嗪，-哌啶，-吡嗪并吡啶并吲哚和-吡嗪并异喹啉，并在分离的豚鼠中研究了它们的H1-拮抗活性。回肠。定量的构效关系分析表明，这些化合物侧链的疏水性在其活性中起主要作用，而空间和电子因素则次要。所有这些化合物都作用于共同的受体，并似乎与该受体发生类似的相互作用。
Synthesis of some substituted pyrazinopyridoindoles and 3D QSAR studies along with related compounds: Piperazines, piperidines, pyrazinoisoquinolines, and diphenhydramine, and its semi-rigid analogs as antihistamines (H1)

作者：Mridula Saxena、Stuti Gaur、Philip Prathipati、Anil K. Saxena

DOI：10.1016/j.bmc.2006.09.018

日期：2006.12

QSAR studies on the title compounds led to the development of a model with three biophoric sites and six secondary sites viz. H-acceptor (ACC), H-donor (DON), heteroatom (presence), hydrophobic (hydrophobicity), steric (refractivity), and a ring (presence) along with total hydrophobicity and total refractivity as global properties. The model predicted the test set of compounds reasonably well. Three of

对标题化合物的3D QSAR研究导致开发了一个具有三个生化位点和六个次要位点的模型。H-受体（ACC），H-供体（DON），杂原子（存在），疏水性（疏水性），空间（折射率）和环（存在性）以及总的疏水性和总折射率作为全局属性。该模型可以很好地预测化合物的测试集。五个新合成的2取代的octahydropyrazinopyridoindoles中的三个已显示出有效的抗组胺性H（1）活性，具有较低的毒性和镇静作用。
HDAC6 inhibitors and their uses

申请人：Universität Regensburg

公开号：US10106540B2

公开（公告）日：2018-10-23

The present invention relates to small molecule compounds and their use as HDAC inhibitors and in the treatment of various diseases, such as cancer. The present invention further relates to methods of synthesizing the compounds and methods of treatment. H-L(HA), H is a head group selected from (head group 1), (head group 2), (head group 3), (head group 4), (head group 5) and (head group 6).

本发明涉及小分子化合物及其作为 HDAC 抑制剂和治疗各种疾病（如癌症）的用途。本发明进一步涉及合成化合物的方法和治疗方法。H-L（HA），H 是选自（头组 1）、（头组 2）、（头组 3）、（头组 4）、（头组 5）和（头组 6）的头组。
Rao, Jyoti; Saxena, Anil K.; Saxena, R. M., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1987, vol. 26, # 1-12, p. 761 - 765

作者：Rao, Jyoti、Saxena, Anil K.、Saxena, R. M.、Singh, H. K.、Kar, K.、Srimal, R. C.

DOI：——

日期：——
A Convenient Method for Indole<i>N</i>-Alkylation in Substituted Pyrazino[2′,1′:6,1]pyrido[3,4-<i>b</i>]indoles

作者：Shiv K. Agarwal、Anil K. Saxena、Nitya Anand

DOI：10.1055/s-1981-29487

日期：——