98809-69-9

Upstream product

• 50-00-0 formaldehyd 
• 36455-21-7 3-benzyloxy-4-methoxyphenylethylamine 
• 109849-38-9 N-formyl-6-benzyloxy-7-methoxy-1,2,3,4-tetrahydroisoquinoline 
• 63909-29-5 3-benzyloxy-4-methoxy-β-nitrostyrene 
• 55161-43-8 N-{2-[3-(benzyloxy)-4-methoxyphenyl]ethyl}acetamide 
• 63909-28-4 2-(3'-benzyloxy-4'-methoxyphenyl)-1-nitroethane 
• 124066-12-2 N-acetyl-1,2,3,4-tetrahydroisoquinoline 
• 1064206-87-6 6-benzyloxy-4-hydroxy-7-methoxy-1,2,3,4-tetrahydroisoquinoline 
• 63909-29-5 (E)-2-(benzyloxy)-1-methoxy-4-(2-nitrovinyl)benzene 
• 2426-87-1 3-methoxy-4-(phenylmethoxy)benzaldehyde 
• 1064206-86-5 N-(4-benzyloxy-3-methoxybenzyl)-N-(2,2-diethoxyethyl)amine 
• 100-44-7 benzyl chloride 
• 621-59-0 isovanillin 
• 6346-05-0 3-benzyloxy-4-methoxybenzaldehyde 

Downstream Products

• 116195-54-1 (S)-valino tert-butyl ether formamidine of 3-benzyloxy-4-methoxy-1,2,3,4-tetrahydro-isoquinoline 
• 68360-22-5 6-(benzyloxy)-7-methoxy-3,4-dihydroisoquinoline 
• 125198-35-8 6-(Benzyloxy)-2-hydroxy-7-methoxy-1-<2,3-(methylenedioxy)benzyl>-1,2,3,4-tetrahydroisoquinoline 
• 911057-03-9 adamantan-1-yl-(6-benzyloxy-7-methoxy-3,4-dihydro-1H-isoquinolin-2-yl)-methanone 
• 508237-04-5 5-Amino-8-(6-benzyloxy-7-methoxy-1,2,3,4-tetrahydroisoquinolin-2-ylmethyl)-2-(2-furyl)[1,2,4]triazolo[1,5-c]pyrimidine 
• 1064201-17-7 6-benzyloxy-7-methoxy-2-(3-methoxyphenylsulfonyl)-1,2,3,4-tetrahydroisoquinoline 
• 1064206-84-3 6-benzyloxy-7-methoxy-2-(2,4,6-trimethoxybenzoyl)-1,2,3 ,4-tetrahydroisoquinoline 
• 1064198-02-2 6-benzyloxy-7-methoxy-2-(2,3,4-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline 
• 1064198-09-9 6-(benzyloxy)-7-methoxy-2-(3,4,5-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline 
• 1064198-42-0 6-hydroxy-7-methoxy-2-(3-methoxybenzyl)-1,2,3,4-tetrahydroisoquinoline 
• 1064199-11-6 2-benzyl-7-methoxy-6-sulfamoyloxy-1,2,3,4-tetrahydroisoquinoline 
• 1064199-12-7 7-methoxy-2-(2-methoxybenzyl)-6-sulfamoyloxy-1,2,3,4-tetrahydroisoquinoline 
• 1064199-06-9 7-methoxy-2-(3-methoxybenzyl)-6-sulfamoyloxy-1,2,3,4-tetrahydroisoquinoline 
• 1064199-08-1 7-methoxy-2-(4-methoxybenzyl)-6-sulfamoyloxy-1,2,3,4-tetrahydroisoquinoline 

Relevant academic research and scientific papers

RHODIUM CATALYZED HYDROGENATION OF NITROGEN HETEROAROMATICS UNDER WATER GAS SHIFT CONDITIONS. SELECTIVE SYNTHESIS OF 1,2,3,4-TETRAHYDROQUINOLINES AND N-FORMYL-1,2,3,4-TETRAHYDROISOQUINOLINES

Quinolines and isoquinolines are hydrogenated selectively in the nitrogen-containing ring by means of carbon monoxide and water in the presence of catalytic amount of rhodium carbonyl cluster.

NOVEL ANTHRANILIC ACID DERIVATIVES

The present invention is directed to a novel compound of Formula 1 wherein the radiolabeled compound of Formula 1 is capable of being used as a radiotracer in PET imaging of a targeted localized tissue and targeted radionuclide therapy of one or more conditions that may be regulated or normalized via inhibition of transporter such as Pgp, BCRP or MRP I. The novel compounds of Formula 1 can also be used as substrates for binding with one or more ABC transporters. In particular, the present invention aids in diagnosis and therapeutic treatment of MDR disorders in all forms of cancers and neurological disorders of the central nervous system. The present invention further provides methods of preparation of compounds of Formula 1 and novel intermediates used in the preparation of compounds of Formula 1.

Tetrahydroisoquinolinone-based steroidomimetic and chimeric microtubule disruptors

A structure-activity relationship (SAR) translation strategy was used for the discovery of tetrahydroisoquinoline (THIQ)-based steroidomimetic and chimeric microtubule disruptors based upon a steroidal starting point. A steroid A,B-ring-mimicking THIQ core was connected to methoxyaryl D-ring ring mimics through methylene, carbonyl and sulfonyl linkers to afford a number of steroidomimetic hits (e.g., 7-methoxy-2-(3- methoxybenzyl)-6-sulfamoyloxy-1,2,3, 4-tetrahydroisoquinoline (20 c) GI50=2.1 μM). Optimisation and control experiments demonstrate the complementary SAR of this series and the steroid derivatives that inspired its design. Linkage of the THIQ-based A,B-mimic with the trimethoxyaryl motif prevalent in colchicine site binding microtubule disruptors delivered a series of chimeric molecules whose activity (GI50=40 nM) surpasses that of the parent steroid derivatives. Validation of this strategy was obtained from the excellent oral activity of 7-methoxy-6-sulfamoyloxy-2-(3,4,5-trimethoxybenzyl)-1,2,3,4- tetrahydroisoquinoline (20 z) relative to a benchmark steroidal bis- sulfamate Copyright

Steroidomimetic tetrahydroisoquinolines for the design of new microtubule disruptors

Structure-activity relationship translation offers an expeditious means for discovery of new active series. This approach was applied to discover tetrahydroisoquinoline (THIQ)-based steroidomimetic microtubule disruptors. The two A-ring elements of a thre

Chimeric microtubule disruptors

A chimeric approach is used to discover microtubule disruptors with excellent in vitro activity and oral bioavailability; a ligand-protein interaction with carbonic anhydrase that enhances bioavailability is characterised by protein X-ray crystallography. Dosing of a representative chimera in a tumour xenograft model confirms the excellent therapeutic potential of the class. The Royal Society of Chemistry 2010.

Synthesis of protoberberines using a silyl-directed Pictet-Spengler cyclization

Five naturally-occurring protoberberines have been synthesized in enantioenriched form by alkylation by two different 2-trimethylsilylbenzyl chlorides of four tetrahydroisoquinolines, derivatized with Meyers' formamidine valinol methyl ether chiral auxiliary. Silyl-directed Pictet-Spengler cyclization of the ensuing 3,4-dimethoxy-2-trimethylsilylbenzyl tetrahydroisoquinolines leads to four of the target protoberberines in excellent yield and complete regioselectivity. In the fifth case, the 3,4-methylenedioxy analog gives a mixture of protoberberine and a product of ring closure at C6 of the benzyl moiety in a 3:4 ratio.

PHELLODENDRINE ANALOGS AND ALLERGY TYPE IV SUPPRESSOR CONTAINING THE SAME AS ACTIVE INGREDIENT

Phellodendrine analogs represented by general formula (I), wherein A represents the group (a); B represents hydrogen, lower alkyl or lower acyl, or alternatively A and B together with the adjacent nitrogen atom form a substituted 1,2,3,4-tetrahydroisoquinoline ring represented by general formula (II), R11, R12, R21, R22, R31 and R32 represent each hydrogen, hydroxyl or lower alkoxy; n1 represents a number of 0 to 2; n2 represents a number of 1 and 2; and m1 represents a number of 0 to 1, provided tsat when A represents the group (b), and n2 is 2, B is lower acyl, and that when A and B together form a substituted 1,2,3,4-tetrahydroisoquinoline ring, n1 is 1 and m1 is not 0. These analogs (I) and related compounds have an excellent activity of suppressing allergy type IV and hence are utilizable as a medicine efficacious against diseases wherein allergy type IV participates, such as chronic hepatitis, intractable asthma, nephrotic syndrome or rheumatism.

Rhodium catalyzed hydrogenation of quinolines and isoquinolines under water-gas shift conditions

Wide variety of quinolines and isoquinolines can be hydrogenated selectively in the nitrogen-containing ring by means of carbon monoxide and water in the presence of catalytic amount of rhodium carbonyl cluster. These reactions provide a useful method for the preparation of 1,2,3,4-tetrahydroquinolines and 1,2,3,4-tetrahydroisoquinolines which are key intermediates for the synthesis of isoquinoline alkaloids and other biologically active nitrogen compounds.