CAS: 42923-77-3; 6-Methoxy-1,2,3,4-Tetrahydroisoquinoline

该化合物是化学化合物,其特征是双环结构,其中包括四氢索基尼松框架,在6个位置上有一个甲氧基组,该化合物一般被归类为碱类,由于潜在的生物活动,对药用化学感兴趣.甲基氧组的存在可影响其药理特性,包括溶性及受体结合性.该化合物经常被研究其对...

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57196-62-0 43207-78-9 1745-05-7

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合成工艺路线路线简述

  • 合成目标产物 6-Methoxy-1,2,3,4-Tetrahydro-Isoquinoline 主要起始原料 Formaldehyde And 3-Methoxyphenethylamine
  • (文献来源)合成步骤主要原料 Formaldehyde 和 3-Methoxyphenethylamine
6-甲氧基异喹啉置于铂 氢气体系中,用 溶剂黄146 作为反应溶剂,化学反应生成 6-甲氧基-1,2,3,4-四氢异喹啉
参考文献:在结构上与1-甲基-4-苯基-1,2,3,6-四氢吡啶(mptp)相关的异喹啉衍生物对复合物i的抑制作用
标题:在结构上与1-甲基-4-苯基-1,2,3,6-四氢吡啶(mptp)相关的异喹啉衍生物对复合物i的抑制作用
摘要:继发于复合物i抑制的线粒体呼吸衰竭可能会导致帕金森氏病(pd)中黑质细胞死亡的神经退行性过程.在结构上与1-甲基-4-苯基-1,2,3,6-四氢吡啶(mptp)或1-甲基-4-苯基吡啶鎓(mpp +)相关的异喹啉衍生物可能是配合物i的抑制剂,并且与病因有关pd作为内源性神经毒素.为了确定异喹啉衍生物抑制线粒体功能的效力和结构要求,我们研究了三类异喹啉衍生物(11种异喹啉,2种二氢异喹啉和9种1,2,3,4-四氢异喹啉)中22种中性和季化合物的作用大鼠前脑线粒体片段中呼吸链酶上的mpp +和mpp +.除去甲萘酚和n,N-丙基异喹啉鎓外,所有化合物均以时间非依赖性但浓度依赖性的方式抑制复合物i,Ic50范围为0.36-22 Mm.与1-甲基-4-苯基吡啶鎓离子(mpp +)(ic50 = 4.1 Mm)相比,几种异喹啉衍生物是更有效的络合物i抑制剂,最有活性的是n-甲基-6-甲氧基-1,2
DOI:10.1016/0006-2952(95)02086-1

海关参考信息

专利信息


专利号:US-6887887-B2
优先权日:2001-03-19
标 题:Asymmetric synthesis of (S,S,R)-(-)-actinonin and its analogs and uses therefor
发明人:BORNMANN WILLIAM G; SIROTNAK FRANCIS; SCHER HOWARD; VIDAL EPHRAIM; BORELLA CHRISTOPHER; SCHEINBERG DAVID
权利人:SLOAN KETTERING INST CANCER
摘要:The present invention provides methods for the asymmetric synthesis of (S,S,R)-(−)-actinonin and its analogs and the compounds thereby synthesized having a structural formula: n n nwhere R 1 is an optionally substituted or halogenated alkyl, aryl, heteroalkyl or heteroaryl amine, said R 1 further comprising a cyclic or bicyclic structure; R 2 is methyl, CH 2 CH 3 , (CH 2 ) 2 CH 3 , C(CH 3 ) 3 , phenyl, 3,4-dichlorophenyl, biphenyl, benzyl, 4-hydroxybenzyl, piperidine, N-Boc-4-piperidine, CH 2 -(N-Boc-4-piperidine), 4-tetrahydropyran, CH 2 -4-tetrahydropyran, 3-methyl indolyl, 2-naphthyl, 3-pyridyl, 4-pyridyl, 3-thienyl; R 3 is R 2 or C 3-8 alkyl, R 4 is C 1-3 alkyl; and R 5 is NH 2 , OH, NHOH, NHOCH 3 , N(CH 3 )OH, N(CH 3 )OCH 3 , NHCH 2 CH 3 , NH(CH 2 CH 3 ), NHCH 2 (2,4-(OCH3) 2 Ph, NHCH 2 (4-NO 2 )Ph, NHN(CH 3 ) 2 , proline, or 2-hydroxymethyl pyrrolidine. Additionally, a method for the treatment of a neoplastic disease or for the inhibition of tumor cell growth each comprising the step of administering to an individual in need of such treatment a pharmacologically effective dose of the compounds of the present invention are provided.

专利号:US-7872138-B2
优先权日:2006-08-07
标 题 :Process for the preparation of substituted-1,2,3,4-tetrahydroisoquinoline derivatives
发明人:VILLANI FRANK J; ZHONG HUA
权利人:JANSSEN PHARMACEUTICA NV
摘要:The present invention is directed to a process for the synthesis of substituted-1,2,3,4-tetrahydroisoquinoline derivatives, useful as intermediates in the synthesis of pharmaceutical agents.

专利号:US-9458111-B2
优先权日:2010-07-29
标题:Process for the synthesis of substituted urea compounds
发明人:LEARMONTH DAVID ALEXANDER; BROADBELT BRIAN; WAHNON JORGE BRUNO REIS
权利人:LEARMONTH DAVID ALEXANDER; BROADBELT BRIAN; WAHNON JORGE BRUNO REIS; BIAL—PORTELA & CA S A
摘要:A process for preparing a substitute urea of Formula (II) or Formula (I), or a pharmaceutically acceptable salt or ester thereof: n nthe process comprising the reaction of a carbamate of Formula (II′): Formula (I′):n n nwith a primary or secondary amine of the formula R1R2NH, wherein ring A, and R1, R2, R5, V, W, X, Y and Z are as defined herein.

专利号:US-12435094-B1
优先权日:2024-11-12
标题:Methods of preparing isomers, analogs, and synthetic derivatives from akuamma seeds
发明人:MITCHELL HAYWOOD MAX; PAGE CECIL; MERINO JOSEPH WILLIAM
权利人:MITCHELL HAYWOOD MAX; PAGE CECIL; MERINO JOSEPH WILLIAM
摘要:Methods are provided for the extraction, isolation, and synthesis of akuammine and other naturally occurring alkaloids from the seeds of the plant Picralima nitida (Akuamma), and their conversion to a variety of isomers, analogs, and synthetic derivatives.

专利号:US-2015197503-A1
优先权日:2012-07-27
标题 :Process for the synthesis of substituted urea compounds
发明人:RUSSO DOMENICO; WAHNON JORGE BRUNO REIS; MATON WILLIAM; ESZENYI TIBOR
权利人:BIAL PORTELA & Cª S A
摘要:A process for preparing a substituted urea compound of Formula II or Formula I, or a pharmaceutically acceptable salt or ester thereof, Formula II, Formula I the process comprising the reaction of an intermediate of Formula II′ or Formula 1′, Formula II′, Formula I′ with a carbamoyl halide of the formula: R1R2NC(=0)Hal, in a solvent consisting essentially of pyridine, wherein Hal represents Cl, F, I or Br, and wherein ring A, and R1, R2, R5, V, W, X, Y and Z are as defined herein.

专利号:US-2005272667-A1
优先权日:2001-03-19
标题:Analogs and derivatives of (S,S,R)-(-)-actinonin and uses therefor
发明人:SCHEINBERG DAVID; BORNMANN WILLIAM G; SIROTNAK FRANCIS; SCHER HOWARD; VIDAL EPHRAIM; BORELLA CHRISTOPHER
权利人:SCHEINBERG DAVID; BORNMANN WILLIAM G; SIROTNAK FRANCIS; SCHER HOWARD; VIDAL EPHRAIM; BORELLA CHRISTOPHER
摘要:The present invention provides analog and derivative compounds of (S,S,R)-(−)-actinonin and methods of asymmetric synthesis thereof having a structure: n n nwhere R 1 is hydrogen, C(O)R 6 or R 1 in combination with N is 2-oxomorpholine, R 2 is hydrogen, methyl, CH 2 CH(CH 3 ) 2 , (CH 2 ) 2 CH 3 , CH(CH 3 ) 2 , (CH 2 ) 3 CH 3 , (CH 2 ) 4 NH 2 , (CH 2 ) 3 CO 2 H, phenyl, 3,4-dichlorophenyl, biphenyl, benzyl, 4-hydroxybenzyl, piperidine, N-Boc-4-piperidine, CH 2 -(N-Boc-4-piperidine), 4-tetrahydropyran, CH 2 -4-tetrahydropyran, 3-methyl indolyl, 2-naphthyl, 3-pyridyl, 4-pyridyl, 3-thienyl, R 3 is R 2 or C 3-8 alkyl, R 4 is C 1-3 alkyl, R 5 is NH 2 , OH, NHOH, NHOCH 3 , N(CH 3 )OH, N(CH 3 )OCH 3 , NHCH 2 CH 3 , NH(CH 2 CH 3 ), NHCH 2 (2,4-(OCH 3 ) 2 Ph, NHCH 2 (4-NO 2 )Ph, NHN(CH 3 ) 2 , proline, or 2-hydroxymethyl pyrrolidine and R 6 is an optionally substituted or halogenated alkyl, aryl, heteroalkyl or heteroaryl amine where R 6 further comprising a cyclic or bicyclic structure. Also provided are methods for treating a neoplastic disease or for inhibiting tumor cell growth using the compounds present invention or using the compound (S,S,R)-(−)-actinonin.
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主要参考文献

参考标题:Ruthenium-Catalyzed Oxidative Formal Aza-Diels-Alder Reaction: Enantioselective Synthesis Of Benzo[A ]Quinolizine-2-Ones
作者:Yuan Yao,Hai-Jie Zhu,Fang Li,Cheng-Feng Zhu,Yun-Fei Luo,Xiang Wu,Eric Assen B. Kantchev |发布日期:2017.9.18
摘要:11Bs)‐benzo[a]Quinolizine‐2‐one Derivatives In Good Enantio‐ And Diastereoselectivity By A One‐pot Oxidative Formal Aza‐diels-Alder Reaction Of 1,2,3,4‐tetrahydroisoquinolines And α,β‐unsaturated Ketones Is Described. The Reaction Proceeds Via Tandem Ruthenium‐catalyzed Amine Dehydrogenation Using Tert‐butyl Hydroperoxide (Tbhp) As The Oxidant And A Chiral Thiourea‐catalyzed Formal Aza‐[4+2] Cycloaddition, Providing

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摘要:Structure et Activite Pharmacodyanmique des Medicaments du Systeme Nerveux Vegetatif, Bovet, D., and F. Bovet-Nitti, New York, S. Karger, 1948, -(244), 1948
摘要:Álvarez, M.; Joule, J. A., Science of Synthesis, (2005) 15, 677.
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