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N-oxiranylmethyl-1,2,3,4-tetrahydrocarbazole | 77233-17-1

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

N-oxiranylmethyl-1,2,3,4-tetrahydrocarbazole

英文别名

9-oxiranylmethyl-2,3,4,9-tetrahydro-1H-carbazole；9-(2,3-epoxypropyl)-2,3,4,9-tetrahydro-1H-carbazole；9-(oxiran-2-ylmethyl)-2,3,4,9-tetrahydro-1H-carbazole；9-(oxiran-2-ylmethyl)-1,2,3,4-tetrahydrocarbazole

N-oxiranylmethyl-1,2,3,4-tetrahydrocarbazole化学式

CAS

77233-17-1

化学式

C₁₅H₁₇NO

mdl

——

分子量

227.306

InChiKey

HPEFFMHRKFBRLQ-UHFFFAOYSA-N

BEILSTEIN

——

EINECS

——

物化性质

熔点：

34-36 °C
沸点：

410.0±25.0 °C(Predicted)
密度：

1.28±0.1 g/cm3(Predicted)

计算性质

辛醇/水分配系数(LogP)：

2.9
重原子数：

17
可旋转键数：

2
环数：

4.0
sp3杂化的碳原子比例：

0.47
拓扑面积：

17.5
氢给体数：

0
氢受体数：

1

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
1,2,3,4-四氢咔唑	1,2,3,4-tetrahydrocarbazole	942-01-8	C₁₂H₁₃N	171.242

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	1,3-bis(1,2,3,4-tetrahydro-9H-carbazol-9-yl)-2-propanol	343805-70-9	C₂₇H₃₀N₂O	398.548
——	1-(butylamino)-3-(1,2,3,4-tetrahydro-9H-carbazol-9-yl)-2-propanol	1346265-08-4	C₁₉H₂₈N₂O	300.444
——	1-(benzylamino)-3-(1,2,3,4-tetrahydro-9H-carbazol-9-yl)-2-propanol	300590-63-0	C₂₂H₂₆N₂O	334.461
——	1-(cyclopentylamino)-3-(1,2,3,4-tetrahydro-9H-carbazol-9-yl)-2-propanol	1346265-09-5	C₂₀H₂₈N₂O	312.455
——	1-(1-pyrrolidinyl)-3-(1,2,3,4-tetrahydro-9H-carbazol-9-yl)-2-propanol	1346265-12-0	C₁₉H₂₆N₂O	298.428
——	1-(4-methylbenzylamino)-3-(1,2,3,4-tetrahydro-9H-carbazol-9-yl)-2-propanol	1346265-16-4	C₂₃H₂₈N₂O	348.488
——	1-(1-piperidinyl)-3-(1,2,3,4-tetrahydro-9H-carbazol-9-yl)-2-propanol	5679-70-9	C₂₀H₂₈N₂O	312.455
——	1-(phenylamino)-3-(1,2,3,4-tetrahydro-9H-carbazol-9-yl)-2-propanol	1346265-10-8	C₂₁H₂₄N₂O	320.434
——	1-(hexahydro-1H-azepin-1-yl)-3-(1,2,3,4-tetrahydro-9H-carbazol-9-yl)-2-propanol	1346265-13-1	C₂₁H₃₀N₂O	326.482
——	9-[2-methoxy-3-(1-piperidinyl)propyl]-2,3,4,9-tetrahydro-1H-carbazole	1346265-07-3	C₂₁H₃₀N₂O	326.482
——	1-(3-methylbenzylamino)-3-(1,2,3,4-tetrahydro-9H-carbazol-9-yl)-2-propanol	1346265-15-3	C₂₃H₂₈N₂O	348.488
——	1-(4-chlorobenzylamino)-3-(1,2,3,4-tetrahydro-9H-carbazol-9-yl)-2-propanol	1346265-30-2	C₂₂H₂₅ClN₂O	368.906
——	1-(4-bromobenzylamino)-3-(1,2,3,4-tetrahydro-9H-carbazol-9-yl)-2-propanol	1346265-33-5	C₂₂H₂₅BrN₂O	413.357
——	1-[(3-pyridylmethyl)amino]-3-(1,2,3,4-tetrahydro-9H-carbazol-9-yl)-2-propanol	1346265-38-0	C₂₁H₂₅N₃O	335.449
——	1-(2-methylbenzylamino)-3-(1,2,3,4-tetrahydro-9H-carbazol-9-yl)-2-propanol	1346265-14-2	C₂₃H₂₈N₂O	348.488
——	1-(3-bromobenzylamino)-3-(1,2,3,4-tetrahydro-9H-carbazol-9-yl)-2-propanol	1346265-32-4	C₂₂H₂₅BrN₂O	413.357
——	1-(2-bromobenzylamino)-3-(1,2,3,4-tetrahydro-9H-carbazol-9-yl)-2-propanol	1346265-31-3	C₂₂H₂₅BrN₂O	413.357
——	1-(3-chlorobenzylamino)-3-(1,2,3,4-tetrahydro-9H-carbazol-9-yl)-2-propanol	1346265-29-9	C₂₂H₂₅ClN₂O	368.906
——	1-(1,2,3,4-tetrahydro-9H-carbazol-9-yl)-3-[4-(trifluoromethyl)benzylamino]-2-propanol	1346265-36-8	C₂₃H₂₅F₃N₂O	402.46
——	1-(4-methoxybenzylamino)-3-(1,2,3,4-tetrahydro-9H-carbazol-9-yl)-2-propanol	1346265-21-1	C₂₃H₂₈N₂O₂	364.488
——	1-(2-chlorobenzylamino)-3-(1,2,3,4-tetrahydro-9H-carbazol-9-yl)-2-propanol	1346265-28-8	C₂₂H₂₅ClN₂O	368.906
——	1-(2,6-difluorobenzylamino)-3-(1,2,3,4-tetrahydro-9H-carbazol-9-yl)-2-propanol	1346265-43-7	C₂₂H₂₄F₂N₂O	370.442
——	1-[4-[(E)-3-phenylprop-2-enyl]piperazin-1-yl]-3-(1,2,3,4-tetrahydrocarbazol-9-yl)propan-2-ol	1067275-03-9	C₂₈H₃₅N₃O	429.605
——	1-(1-methyl-1-phenylethylamino)-3-(1,2,3,4-tetrahydro-9H-carbazol-9-yl)-2-propanol	1346265-11-9	C₂₄H₃₀N₂O	362.515
——	1-(2,4-difluorobenzylamino)-3-(1,2,3,4-tetrahydro-9H-carbazol-9-yl)-2-propanol	1346265-41-5	C₂₂H₂₄F₂N₂O	370.442
——	1-(2,5-difluorobenzylamino)-3-(1,2,3,4-tetrahydro-9H-carbazol-9-yl)-2-propanol	1346265-42-6	C₂₂H₂₄F₂N₂O	370.442
——	1-(3-methoxybenzylamino)-3-(1,2,3,4-tetrahydro-9H-carbazol-9-yl)-2-propanol	1346265-19-7	C₂₃H₂₈N₂O₂	364.488
——	1-(1,2,3,4-tetrahydro-9H-carbazol-9-yl)-3-[3-(trifluoromethyl)benzylamino]-2-propanol	1346265-35-7	C₂₃H₂₅F₃N₂O	402.46
——	1-(2,6-dichlorobenzylamino)-3-(1,2,3,4-tetrahydro-9H-carbazol-9-yl)-2-propanol	1346265-44-8	C₂₂H₂₄Cl₂N₂O	403.351
——	1-(2-methoxybenzylamino)-3-(1,2,3,4-tetrahydro-9H-carbazol-9-yl)-2-propanol	1346265-17-5	C₂₃H₂₈N₂O₂	364.488

反应信息

作为反应物：

描述：

N-oxiranylmethyl-1,2,3,4-tetrahydrocarbazole 在盐酸作用下，以水、异丙醇、丙酮为溶剂，反应 10.0h，生成 1-(3,5-dimethyladamantan-1-ylamino)-3-(1,2,3,4-tetrahydrocarbazol-9-yl)propan-2-ol hydrochloride

参考文献：

名称：

Molecular design of multitarget neuroprotectors 3. Synthesis and bioactivity of tetrahydrocarbazole—aminoadamantane conjugates

摘要：

提出了一种合成方法，用于设计新的多靶点神经保护剂，该方法结合了四氢咔唑和氨基亚氨基叔丁基药物核心片段，通过2-羟基丙烯间隔体与9-氧杂基甲基-2,3,4,9-四氢-1H-咔唑和氨基亚氨基叔丁基反应，合成了1-(亚氨基-1-丙基)-3-(1,2,3,4-四氢咔唑-9-基)-丙-2-醇。研究了合成化合物对神经元NMDA受体和大鼠肝线粒体功能特性的影响。

DOI：

10.1007/s11172-016-1461-5
作为产物：

描述：

1,2,3,4-四氢咔唑、环氧溴丙烷在 potassium hydroxide 作用下，以 N,N-二甲基甲酰胺为溶剂，反应 7.0h，以65%的产率得到N-oxiranylmethyl-1,2,3,4-tetrahydrocarbazole

参考文献：

名称：

Molecular design of multitarget neuroprotectors 3. Synthesis and bioactivity of tetrahydrocarbazole—aminoadamantane conjugates

摘要：

提出了一种合成方法，用于设计新的多靶点神经保护剂，该方法结合了四氢咔唑和氨基亚氨基叔丁基药物核心片段，通过2-羟基丙烯间隔体与9-氧杂基甲基-2,3,4,9-四氢-1H-咔唑和氨基亚氨基叔丁基反应，合成了1-(亚氨基-1-丙基)-3-(1,2,3,4-四氢咔唑-9-基)-丙-2-醇。研究了合成化合物对神经元NMDA受体和大鼠肝线粒体功能特性的影响。

DOI：

10.1007/s11172-016-1461-5

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文献信息

Synthesis of 9-substituted 2,3,4,9-tetrahydro-1H-carbazole derivatives and evaluation of their anti-prion activity in TSE-infected cells

作者：Tsutomu Kimura、Junji Hosokawa-Muto、Kenji Asami、Toshiaki Murai、Kazuo Kuwata

DOI：10.1016/j.ejmech.2011.08.039

日期：2011.11

a variety of GJP14 derivatives were prepared using pyrrole derivatives, (haloalkyl)oxiranes, and amines, and their anti-prion activity was evaluated in TSE-infected cells. It was found that the tricyclic aromatic ring, a hydroxy group at the 2-position and an amino group at the 3-position of the N-propyl group were the basic requirements for anti-prion activity. The derivatives bearing an N-ortho-halobenzyl

2,3,4,9-四氢-9- [2-羟基-3-（1-哌啶基）丙基] -6-甲基-1 H-咔唑-1-酮（GJP14）是一种新型的抗-病毒化合物，我们之前是通过计算机筛选和细胞分析发现的。在这项研究中，使用吡咯衍生物，（卤代烷基）氧杂环丁烷和胺制备了多种GJP14衍生物，并在TSE感染的细胞中评估了它们的抗-病毒活性。发现三环芳环，N-丙基的2-位羟基和3-位的氨基是抗-病毒活性的基本要求。衍生物轴承的ñ -邻-卤代苄基具有更高的活性，最有效的衍生物是原始的先导化合物GJP14的8倍。
Synthesis and structure–activity relationship studies of 1,3-disubstituted 2-propanols as BACE-1 inhibitors

作者：Arun Babu Kumar、Jordan Micheal Anderson、Anthony Lester Melendez、Roman Manetsch

DOI：10.1016/j.bmcl.2012.05.072

日期：2012.7

A library of 1,3-disubstituted 2-propanols was synthesized and evaluated as low molecular weight probes for beta-secretase inhibition. By screening a library of 121 1,3-disubstituted 2-propanol derivatives, we identified few compounds inhibiting the enzyme at low micromolar concentrations. The initial hits were optimized to yield a potent BACE-1 inhibitor exhibiting an IC50 constant in the nanomolar range. Exploration of the pharmacological properties revealed that these small molecular inhibitors possessed a high selectivity over cathepsin D and desirable physicochemical properties beneficial to cross the blood-brain barrier. (C) 2012 Elsevier Ltd. All rights reserved.
Structure–activity relationship studies of the chromosome segregation inhibitor, Incentrom A

作者：Hee-Yoon Lee、Yongsik Jung、Wonyeob Kim、Jin Hee Kim、Min-Soo Suh、Seung Koo Shin、Hye-Joo Yoon

DOI：10.1016/j.bmcl.2008.07.006

日期：2008.8

A series of Incentrom A analogs that inhibit the chromosome segregation process in yeast were synthesized and tested for their effects on chromosome stability and cell proliferation. Pharmacophore and structure-activity relationship of Incentrom A for the anti-yeast activity were established. (C) 2008 Elsevier Ltd. All rights reserved.
Giancaspro; Pizzorno; Albonico, Il Farmaco, 1989, vol. 44, # 5, p. 483 - 493

作者：Giancaspro、Pizzorno、Albonico、Bindstein、Garofalo、Zeichen

DOI：——

日期：——
ZHEREBTSOV I. P.; LOPATINSKIJ V. P.; ROVKINA N. M.; KATERINICH T. P., IZV. VUZOV. XIMIYA I XIM. TEXNOL., 1980, 23, HO 10 1291-1294

作者：ZHEREBTSOV I. P.、 LOPATINSKIJ V. P.、 ROVKINA N. M.、 KATERINICH T. P.

DOI：——

日期：——