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5-氯-2-甲基-3-(1,2,3,6-四氢-4-吡啶基)-1H-吲哚 | 54635-62-0

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

5-氯-2-甲基-3-(1,2,3,6-四氢-4-吡啶基)-1H-吲哚

中文别名

——

英文名称

5-chloro-2-methyl-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole

英文别名

EMD-386088；5-chloro-2-methyl-3-(1,2,3,6-tetrahydro-pyridin-4-yl)-indole；4-(5'-chloro-2'-methyl-3'-indolyl)-1,2,5,6-tetrahydropyridine

CAS

54635-62-0

化学式

C₁₄H₁₅ClN₂

mdl

——

分子量

246.739

InChiKey

BPPGPYJBCVXILI-UHFFFAOYSA-N

BEILSTEIN

——

EINECS

——

物化性质

沸点：

438.1±45.0 °C(Predicted)
密度：

1.242±0.06 g/cm3(Predicted)

计算性质

辛醇/水分配系数(LogP)：

2.8
重原子数：

17
可旋转键数：

1
环数：

3.0
sp3杂化的碳原子比例：

0.29
拓扑面积：

27.8
氢给体数：

2
氢受体数：

1

安全信息

海关编码：

2933990090
储存条件：

-20°C，干燥

SDS

SDS：acab6faeac0e03c7299eb89130dba39d

查看

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
5-氯-2-甲基-3-哌啶-4-基-1H-吲哚	4-(5'-chloro-2'-methyl-3'-indolyl)-piperidine	400801-74-3	C₁₄H₁₇ClN₂	248.755

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	5-chloro-2-methyl-3-(1-methyl-1,2,3,6-tetrahydro-pyridin-4-yl)-indole	55556-45-1	C₁₅H₁₇ClN₂	260.766
——	3-[4-(5-chloro-2-methyl-1H-indol-3-yl)-3,6-dihydropyridin-1(2H)-yl]propyl-1-amine	1365036-48-1	C₁₇H₂₂ClN₃	303.835
——	2-[4-(5-chloro-2-methyl-1H-indol-3-yl)-3,6-dihydropyridin-1(2H)-yl]ethyl-1-amine	1365036-50-5	C₁₆H₂₀ClN₃	289.808
——	tert-butyl 4-(5-chloro-2-methyl-1H-indol-3-yl)-3,6-dihydro-2H-pyridine-1-carboxylate	——	C₁₉H₂₃ClN₂O₂	346.857
——	N-{3-[4-(5-chloro-2-methyl-1H-indol-3-yl)-1,2,3,6-tetrahydropyridin-1-yl]propyl}naphthalene-2-sulfonamide	1365043-93-1	C₂₇H₂₈ClN₃O₂S	494.057
——	N-{4-[4-(5-chloro-2-methyl-1H-indol-3-yl)-1,2,3,6-tetrahydropyridin-1-yl]butyl}naphthalene-2-sulfonamide	1365043-63-5	C₂₈H₃₀ClN₃O₂S	508.084
——	N-{2-[4-(5-chloro-2-methyl-1H-indol-3-yl)-1,2,3,6-tetrahydropyridin-1-yl]ethyl}naphthalene-2-sulfonamide	1365044-11-6	C₂₆H₂₆ClN₃O₂S	480.03
——	N-{3-[4-(5-chloro-2-methyl-1H-indol-3-yl)-1,2,3,6-tetrahydropyridin-1-yl]propyl}-3-methylbenzene-1-sulfonamide	1365044-05-8	C₂₄H₂₈ClN₃O₂S	458.024
——	N-{4-[4-(5-chloro-2-methyl-1H-indol-3-yl)-1,2,3,6-tetrahydropyridin-1-yl]butyl}-3-methylbenzene-1-sulfonamide	1365043-69-1	C₂₅H₃₀ClN₃O₂S	472.051
——	N-{2-[4-(5-chloro-2-methyl-1H-indol-3-yl)-1,2,3,6-tetrahydropyridin-1-yl]ethyl}-3-methylbenzene-1-sulfonamide	1365044-27-4	C₂₃H₂₆ClN₃O₂S	443.997
——	2-{4-[4-(5-chloro-2-methyl-1H-indol-3-yl)-3,6-dihydropyridin-1(2H)-yl]butyl}-1H-isoindole-1,3(2H)-dione	1365036-08-3	C₂₆H₂₆ClN₃O₂	447.964
——	2-{3-[4-(5-chloro-2-methyl-1H-indol-3-yl)-3,6-dihydropyridin-1(2H)-yl]propyl}-1H-isoindole-1,3(2H)-dione	1365036-10-7	C₂₅H₂₄ClN₃O₂	433.937
——	2-{2-[4-(5-chloro-2-methyl-1H-indol-3-yl)-3,6-dihydropyridin-1(2H)-yl]ethyl}-1H-isoindole-1,3(2H)-dione	1365036-12-9	C₂₄H₂₂ClN₃O₂	419.911
——	1-(benzenesulfonyl)-5-chloro-2-methyl-3-(1,2,3,6-tetrahydropyridin-4-yl)indole	1442104-24-6	C₂₀H₁₉ClN₂O₂S	386.902

反应信息

作为反应物：

描述：

5-氯-2-甲基-3-(1,2,3,6-四氢-4-吡啶基)-1H-吲哚在铂作用下，以溶剂黄146 为溶剂，生成 4-(5'-chloro-2'-methyl-3'-indolyl)-piperidine acetate

参考文献：

名称：

(Indolyl-piperidino or

摘要：

该公式化合物的化学式为##SPC1##其中R.sub.1为氢、氯、甲基、甲氧基或三氟甲基，R.sub.2为氢或甲基，R.sub.3为甲基或苯基，R.sub.4和R.sub.5结合形成双键或者在R.sub.1为氯、甲基或三氟甲基的情况下，它们也可以是氢原子。这些化合物及其盐是无毒的、药理学上可接受的酸盐，可用作镇静剂和安定剂。

公开号：

US03980658A1
作为产物：

描述：

5-氯-2-甲基吲哚、 4-piperidone monohydrochloride monohydrate 在磷酸作用下，以溶剂黄146 为溶剂，生成 5-氯-2-甲基-3-(1,2,3,6-四氢-4-吡啶基)-1H-吲哚

参考文献：

名称：

5-氯-2-甲基-3-（1,2,3,6-四氢吡啶-4--4-基）-1 H-吲哚类似物作为5-HT 6受体激动剂的结构-活性关系

摘要：

进一步研究5-羟基色胺6型（5-HT 6）受体激动剂5-氯-2-甲基-3-（1,2,3,6-四氢吡啶-4--4-基）-1 ħ -吲哚（EMD386088，6），一系列的2-甲基-3-（1,2,3,6-四氢吡啶-4-基）-1 ħ -indoles合成，并在体外亲和力，测试了5-HT 6受体的功能活性。我们专注于在吲哚N 1-，2-和5-位上制得的取代基，发现这些取代基不仅会影响5-HT 6上的亲和力受体和内在活性导致拮抗剂，部分激动剂和完全激动剂。为了使化合物表现出有效的5-HT 6受体激动剂特性，吲哚N 1应该未被取代，需要烷基如2-甲基，最后是吲哚5-位的卤素取代基（氟，氯或氯）。溴）是必不可少的要求。然而，在N 1位引入苯磺酰基使完全激动剂6变成5-HT 6受体拮抗剂（30）。2-甲基-3-（1,2,3,6-四氢吡啶-4--4-基）-1 H中的一些化合物还对-吲哚进行脱靶筛选，通常它们

DOI：

10.1016/j.ejmech.2013.03.006

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文献信息

[EN] ARYLOSULFONAMIDES FOR THE TREATMENT OF CNS DISEASES<br/>[FR] ARYLSULFAMIDES POUR LE TRAITEMENT DE MALADIES DU SNC

申请人：ADAMED SP ZOO

公开号：WO2012035123A1

公开（公告）日：2012-03-22

Arylsulphonamide derivatives of formula (I) and pharmaceutically acceptable salts thereof. The compounds may be useful for the treatment and/or prevention of disorders of the central nervous system.

化学式（I）的芳基磺酰胺衍生物及其药用盐。这些化合物可能对中枢神经系统的治疗和/或预防具有用处。
ARYLOSULFONAMIDES FOR THE TREATMENT OF CNS DISEASES

申请人：Kolaczkowski Marcin

公开号：US20130172365A1

公开（公告）日：2013-07-04

Arylsulphonamide derivatives of formula (I) and pharmaceutically acceptable salts thereof. The compounds may be useful for the treatment and/or prevention of disorders of the central nervous system.

化学式（I）的芳基磺胺衍生物及其药用盐。这些化合物可能对中枢神经系统疾病的治疗和/或预防有用。
Novel 3-(1,2,3,6-Tetrahydropyridin-4-yl)-1<i>H</i>-indole-Based Multifunctional Ligands with Antipsychotic-Like, Mood-Modulating, and Procognitive Activity

作者：Adam Bucki、Monika Marcinkowska、Joanna Śniecikowska、Krzysztof Więckowski、Maciej Pawłowski、Monika Głuch-Lutwin、Anna Gryboś、Agata Siwek、Karolina Pytka、Magdalena Jastrzębska-Więsek、Anna Partyka、Anna Wesołowska、Paweł Mierzejewski、Marcin Kołaczkowski

DOI：10.1021/acs.jmedchem.7b00839

日期：2017.9.14

The most troublesome aspects of behavioral and psychological symptoms of dementia (BPSD) are nowadays addressed by antidepressant, anxiolytic, and antipsychotic drugs, often administered off-label. Considering their modest effectiveness in dementia patients, the increased risk of adverse events and cognitive decline, there is an unmet need for well tolerated and effective therapy of BPSD. We designed and synthesized multifunctional ligands characterized in vitro as high affinity partial agonists of D2R, antagonists of 5-HT6R, and blockers of SERT. Moreover, the molecules activated 5-HT1AR and blocked 5-HT7R while having no relevant affinity for off-target M1R and hERG channel. Compound 16 (N-244-(5-chloro-1H-iridol-3-y1)-1,2,3,6-tetrahydropyridin-l-yllethy1}-3-methylbenzene-l-sulfonamide), exhibited a broad antipsychotic-, antidepressant-, and anxiolytic-like activity, not eliciting motor impairments in mice. Most importantly, 16 showed memory-enhancing properties and it ameliorated memory deficits induced by scopolamine. The molecule outperformed most important comparators in selected tests, indicating its potential in the treatment of both cognitive and noncognitive (behavioral and psychological) symptoms of dementia.
2-Alkyl-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indoles as novel 5-HT6 receptor agonists

作者：Cecilia Mattsson、Clas Sonesson、Anna Sandahl、Hartmut E. Greiner、Michael Gassen、Jörg Plaschke、Joachim Leibrock、Henning Böttcher

DOI：10.1016/j.bmcl.2005.06.067

日期：2005.10

A series of 2-alkyl-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indoles were synthesized and evaluated for their 5-HT6 activity. The most potent agonist in this series was 5-chloro-2-methyl-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole with an IC50 = 7.4 nM in H-3-LSD binding and an EC50 = 1.0 nM in a functional assay measuring production of cyclic AMP. (c) 2005 Elsevier Ltd. All rights reserved.
5-HT6 RECEPTOR AND MODULATORS THEREOF FOR THE TREATMENT OF INSULIN-RELATED DISORDERS

申请人：Arena Pharmaceuticals, Inc.

公开号：EP2313769A1

公开（公告）日：2011-04-27