4602-83-9

Usage

Uses

Used in Pharmaceutical Industry:
6,7-DIHYDROXY-3,4-DIHYDROISOQUINOLINE is used as a reagent for the synthesis of 6,7-dihydroxy-3,4-dihydroisoquinline, a novel inhibitor of factor-kB in invitro invasion in murine mammary cells. This application highlights its potential role in the development of new therapeutic agents targeting cancer cell invasion and metastasis.

InChI:InChI=1/C9H9NO2/c11-8-3-6-1-2-10-5-7(6)4-9(8)12/h3-5,10,12H,1-2H2

Relevant academic research and scientific papers

Mellpaladines and dopargimine, novel neuroactive guanidine alkaloids from a Palauan Didemnidae tunicate

Novel guanidine alkaloids dopargimine (1) and mellpaladines A–C (2–4) were isolated from a Palauan Didemnidae tunicate. The structures of 1–4 were elucidated on the basis of spectral data along with chemical reactions. A putative biosynthetic building block of 1–4, 4-guanidinobutyric acid (5), and dimeric polysulfur dopamine, as well as lissoclibadins 11 (6a) and 12 (6b) were also isolated. Compounds 1–3 bound to synaptic receptors, and modulated behavioral profiles of mice after intracerebroventricular injection.

Decahydro-8H-isoquino[2,1-g][1,6]naphthyridine and decahydrobenzo[a]pyrrolo [2,3-e]quinolizine derivatives

Compounds of the formula STR1 wherein: m is an integer of 1-6;n is an integer of 1 or 2;X and Y are independently hydrogen; hydroxy; lower alkyl; lower alkoxy; or halo; or X and Y when adjacent and taken together are methylenedioxy or ethylene-1,2-dioxy;R is STR2 wherein: R 1 and R 2 are independently hydrogen or lower alkyl, or when taken together with the carbon to which they are attached are cycloalkyl;R 3 is hydrogen, lower alkyl, lower alkoxy, hydroxy, trifluoromethyl or halo; and STR3 and pharmaceutically acceptable acid addition salts thereof. The compounds and salts exhibit useful pharmacological properties, including selective α 2 -adrenoceptor antagonist properties and 5-HT 1A receptor partial agonist properties, and are particularly useful for the treatment of sexual dysfunction, depression and anxiety.

Process for the preparation of (8As,12AS,13AS)-decahydroisoquino ((2,1-G) (1,6)-naphthyridin-8-one derivatives

The invention provides a process for preparing single enantiomers of compounds represented by the formula: STR1 and chiral acid addition salts thereof; wherein: X and Y are independently hydrogen; lower alkyl; lower alkoxy; or halo; or X and Y taken together is methylenedioxy or ethylene-1,2-dioxy; which includes reduction of a compound represented by the formula: STR2 to give a mixture of stereoisomers represented by the formula: STR3 wherein each wavy line independently represents a bond in either the α or β position; followed by dissolving the mixture of stereoisomers and a chiral resolving acid in a suitable solvent and allowing the solution to crystallize, giving a salt of the desired enantiomer.

Decahydro-8H-isoquino[2,1-g][1,6]naphthyridine and decahydrobenzo[a]pyrrolo[2,3-e]quinolizine derivatives

Compounds of the formula ψψ ψwherein:ψ X and Y are independently hydrogen; hydroxy; lower alkyl of 1-6 carbon atoms; lower alkoxy of 1-6 carbon atoms; or halo; or X and Y when adjacent and taken together are methylenedioxy or ethylene-1,2-dioxy;ψ R is lower alkyl of 1-6 carbon atoms; cycloalkyl of 3-8 carbon atoms; phenyl or phenyl lower alkyl in which any phenyl group may be optionally substituted by one or two substituents chosen from the group consisting of halo, lower alkyl of 1-4 carbon atoms and lower alkoxy of 1-4 carbon atoms; or -ANHSO2R1; wherein A is lower alkylene of 1-6 carbon atoms; and R1 is lower alkyl of 1-6 carbon atoms or -NRyR3; whereinψ Ry and R3 are independently hydrogen or lower alkyl of 1-6 carbon atoms, or Ry and R3 taken together are cycloalkyl of 3-8 carbon atoms; andψ n is 1 or 2;ψ and the pharmaceutically acceptable salts thereof, are useful as à2-adrenoceptor antagonists, in particular as peripherally selective à2 -adrenoceptor antagonists.ψ