52768-23-7

Usage

Chemical Properties

BEIGE TO BROWN POWDER

InChI:InChI=1/C9H11NO2.BrH/c11-8-3-6-1-2-10-5-7(6)4-9(8)12;/h3-4,10-12H,1-2,5H2;1H

Upstream product

• 2328-12-3 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline monohydrochloride 
• 1745-07-9 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 50-00-0 formaldehyd 
• 645-31-8 3-hydroxytyramine hydrobromide 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 

Downstream Products

• 639468-08-9 3-(6,7-dihydroxy-3,4-dihydro-1H-isoquinolin-2-yl)-1-phenylpropanone 
• 1025057-71-9 4-(4-chlorophenyl)-1-(6,7-dihydroxy-1,2,3,4-tetrahydroisoquinolin-2-yl)butan-1-one 
• 1044872-96-9 N-(4-phenoxybenzoyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline 
• 1044872-90-3 N-(3-phenylbenzoyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline 
• 1044872-92-5 N-(3-pyrid-3-ylbenzoyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline 
• 1044873-00-8 N-(2-phenoxybenzoyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline 
• 1044872-94-7 N-(3-phenoxybenzoyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline 
• 1044873-02-0 N-(5-phenyl-2-furoyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline 

Relevant academic research and scientific papers

BROAD SPECTRUM ANTIVIRAL COMPOSITIONS AND METHODS

Novel thiazole- and isoquinoline- containing compounds are presented that are useful for treating and/or preventing broad-spectrum viral infections. Methods of treating and/or preventing broad-specturm viral infections are also presented. These compounds have shown inhibitio of HCMV, influenza viruses, Zika virus, BK Virus and RSV replication in cell-based assays.

Cephem Compounds with Latent Reactive Groups

Cephem and penem compounds having a styrylmethylene moiety at the 3-position in the cephem or penem ring to which a positively charged leaving group is bonded and wherein the leaving group contains a vicinal diol or is bonded to a unsubstituted or substituted catechol. The leaving group can be a positively charge nitrogen leaving group. Cephems include cephalosporins, cephamycins, carbacephems, and oxacephems. Penems include penems, carbapenems and oxapenems. Preferred cephems are cephalosporins. Preferred penems are carbapenems. Compounds exhibit antibiotic activity against Gram-negative bacteria and/or Gram-positive bacteria. Compounds exhibit antibiotic activity against bacteria which exhibit multi-drug resistance. Compounds of the invention exhibit antibiotic activity against bacterial strains which produce extended spectrum beta-lactamases (ESBL), which produce AmpC beta-lactamases or which produce a carbapenemase. Pharmaceutical compositions comprising one or more cephems or penems or methods of treatment of bacterial infections with such compounds and compositions.

Catechol reactivity: Synthesis of dopamine derivatives substituted at the 6-position

Dopamine is a ubiquitous neurotransmitter essential in the proper functioning of the human body. In addition to this critical role, the catecholamine core has shown utility as a scaffold for numerous drugs and in other applications, like metal detection and adhesive materials. Substituents at the 6-position of dopamine’s catechol core can modulate its stereoelectronic properties, the acidity of its phenolic hydroxyl groups, and the overall hydrophobicity of the molecule. Herein, we report the synthesis of a series of four novel dopamine analogues substituted at the 6-position of catechol core. The1H NMR chemical shift of the aromatic proton meta to the substituent correlated strongly with the Hammett σmconstant, confirming the electronic properties of substituents.

Novel Benzo[a]quinolizidine Analogs Induce Cancer Cell Death through Paraptosis and Apoptosis

Paraptosis is nonapoptotic cell death characterized by massive endoplasmic reticulum (ER)- or mitochondria-derived vacuoles. Induction of paraptosis offers significant advantages for the treatment of chemotherapy-resistant tumors compared with anticancer drugs that rely on apoptosis. Because some natural alkaloids induce paraptotic cell death, a novel series of benzo[a]quinolizidine derivatives were synthesized, and their antiproliferative activity and ability to induce cytoplasmic vacuolation were analyzed. Structural optimization led to the identification of the potent compound 22b, which inhibited cancer cell proliferation in vitro and in vivo and profoundly facilitated paraptosis-like cell death and induced caspase-dependent apoptosis. Further investigation revealed that 22b-mediated vacuolation originated from persistent ER stress and upregulation of LC3B. Paraptosis induced by benzo[a]quinolizidine derivatives thus represents an alternative strategy for cancer chemotherapy.

1-Phenylisoquinoline larvicidal activity against Culex quinquefasciatus

The larvicidal potential of several dopamine 1-phenylisoquinoline derivatives against Culex quinquefasciatus third instar larvae was investigated in a rational search for insecticides. The results showed that these isoquinolines presented moderate larvicidal activity, that the presence of a substituent is needed on carbon 1 for such activity to be presented and that it may be possible to develop novel insecticidal compounds having potential use in controlling insects by appropriate structural modification of 1-phenylisoquinolines. This article presents a possible structure-larvicidal activity relationship for isoquinolinic compounds.

Lamellarins as inhibitors of P-glycoprotein-mediated multidrug resistance in a human colon cancer cell line

Chemical analysis of a Didemnum sp. (CMB-01656) collected during scientific Scuba operations off Wasp Island, New South Wales, yielded five new lamellarins A1 (1), A2 (2), A3 (3), A4 (4) and A5 (5) and eight known lamellarins C (6), E (7), K (8), M (9), S (10), T (11), X (12) and χ (13). Analysis of a second Didemnum sp. (CMB-02127) collected during scientific trawling operations along the Northern Rottnest Shelf, Western Australia, yielded the new lamellarin A6 (14) and two known lamellarins G (15) and Z (16). Structures were assigned to 1-16 on the basis of detailed spectroscopic analysis with comparison to literature data and authentic samples. Access to this unique library of natural lamellarins (1-16) provided a rare opportunity for structure-activity relationship (SAR) investigations, probing interactions between lamellarins and the ABC transporter efflux pump P-glycoprotein (P-gp) with a view to reversing multidrug resistance in a human colon cancer cell line (SW620 Ad300). These SAR studies, which were expanded to include the permethylated lamellarin derivative (17) and a series of lamellarin-inspired synthetic coumarins (19-24) and isoquinolines (25-26), successfully revealed 17 as a promising new non-cytotoxic P-gp inhibitor pharmacophore. Copyright

SAR studies of capsazepinoid bronchodilators. Part 1: The importance of the catechol moiety and aspects of the B-ring structure

Capsazepine as well as its derivatives and analogues are general inhibitors of constriction of human small airways. From a systematic variation of the capsazepine structure, divided into four regions, SARs were established. This part concerns the catechol moiety of the A-ring as well as the 2,3,4,5-tetrahydro-1H-2-azepine moiety (the B-ring) of capsazepine. It is revealed that a conformational constrain (as a fused ring) is important and that compounds with a six-membered B-ring (as a 1,2,3,4-tetrahydroisoquinoline) in general are more potent than the corresponding isoindoline, 2,3,4,5-tetrahydro-1H-2-benzazepine and 2,3,4,5-tetrahydro-1H-3-benzazepine derivatives.

BRONCHORELAXING ARYLAMIDES

The invention relates to novel molecules having the general formula (I), and which molecules are useful to manufacture a medicament to treat a disorder or disease characterized by bronchoconstriction.

Bronchorelaxing agents based on indol- and isoquinoline derivatives

A compound of formula (I) and its acid addition salts, wherein R1-FIj are H, lower (CrC6) alkyl; halogen; NR5R6, wherein R5, R6 are H, lower alkyl, C2-C6 acyl, SO2R7, wherein R7 is lower alkyl, CF3, aryl, substituted aryl; CN; COR8, wherein R8 is H, OH, lower alkyl, lower alkoxy; SO2R9, wherein R9 is OR10, wherein R10 is H, lower alkyl or NRnR12, wherein R11 and R12 is H or lower alkyl; ORi3, wherein R13 is H, lower alkyl, C2-C6 acyl, C1-C8 carboxy, C1-C8 carbamoyl; X is O or S; A is H, lower alkyl; B is C1-C18 alkyl optionally substituted; M is zero or 1; with the proviso that no more than three of R1-R4 are H, for treating and preventing bronchoconstructive pulmonary disease.