82985-09-9

Upstream product

• 2338-18-3 2-aminoindane hydrochloride 
• 138006-38-9 N-(indan-2-yl)propionamide 
• 254885-62-6 5-amino-2-propionamidoindan 
• 107-10-8 propylamine 
• 615-13-4 2-indanone 
• 24445-44-1 N-Methyl-2-aminoindane 
• 556-53-6 N-propylamine hydrochloride 

Downstream Products

• 254885-67-1 2-amino-6-(N,N-di-n-propylamino)thiazolo[4,5-f]indan 

Relevant academic research and scientific papers

Synthesis of Bitopic Ligands as Potent Dopamine D2 Receptor Agonists

In this study, we designed and synthesized twelve bitopic ligands as dopamine D2 receptor (D2R) agonists. The forskolin-induced cAMP accumulation assay revealed that all the finial compounds are able to activate D2R. Furthermore, bitopic ligand N-((trans)-4-(((2,3-dihydro-1H-inden-2-yl)(propyl)amino)methyl)cyclo-hexyl)-1H-pyrrolo[2,3-b]pyridine-2-carboxamide (11 b) showed 21-fold higher potency than lead compound propyl aminoindane (2) and 17-fold higher subtype selectivity for D2R over D4R, indicating that the optimal length of spacer affects the D2R functionality. Molecular modeling study exhibited that 11 b formed an electrostatic interaction and two H-bonds with amino acid Asp114, which contributes significantly to the D2R functional activity. Taken together, we discovered a bitopic ligand 11 b as potent D2R agonist, which may be used as a tool compound for further study.

2-aminothiazol-fused 2-aminoindans and 2-aminotetralins and their use

The invention relates to 2-aminothiazol-fused 2-aminoindans and 2-aminotetralins having general formula (1): wherein R1and R2, which may be identical or different, are selected from the group consisting of a hydrogen atom, alkyl or haloalkyl groups of 1 to 7 carbon atoms, (alkyl)cycloalkyl groups of 3 to 7 carbon atoms, alkenyl or alkynyl groups of 3 to 6 carbon atoms, arylalkyl having 1 to 3 carbon atoms in the alkyl moiety, while the aryl nucleus may be substituted; and n and m are 1 or 2; and the enantiomers and the acid addition salts thereof, pharmaceutical compositions containing them and their use in the preparation of medicaments having an effect on the dopaminergic system of the central nervous system and/or the circulation.

Thiazoloindans and thiazolobenzopyrans: A novel class of orally active central dopamine (partial) agonists

The 2-aminothiazole moiety has proven its value in medicinal chemistry as a stable and lipophilic bioisosteric replacement of a phenol group. This approach has provided dopamine (DA) agonists with good oral availability. To further explore its use in the development of DA agonists, we have combined the 2-aminothiazole moiety with 2-aminoindans and 3-aminobenzopyrans, which are known templates for DA agonists. In this study we have synthesized 6-amino-3-(N,N-di-n-propylamino)-3,4-dihydro-2H-thiazolo[5,4-f]-[1]benzopyran (12) and 6-amino-2-(N,N-di-n-propylamino)thiazolo[4,5-f]indan (20) and several analogues (13, 17, and 21). The affinity of the thiazolobenzopyrans and thiazoloindans for DA receptors was evaluated, which revealed compound 20 to have high affinity for DA D3 receptors. In addition, the compounds were screened for their potential to inhibit lipid peroxidation, to determine their radical scavenging properties. Compounds 12, 20, and 21 were subjected to further pharmacological evaluation in a functional assay to determine intrinsic activity. Compound 20 was also studied with microdialysis (to determine effects on DA turnover in striatum) and in unilaterally 6-OH-DA lesioned rats (to determine their potential as DA agonists). These studies selected compound 20 (GMC 1111) as particularly interesting. Compound 20 caused a rotation activation in unilaterally 6-OH-DA lesioned rats and an increase in DA turnover in rat striatum. This dual agonist/antagonist action is best accounted for by its partial agonism at striatal DA D2 receptors. Interestingly, 20 displayed long-lasting activity and excellent oral availability in 6-OH-DA lesioned rats, making this compound potentially useful for the treatment of Parkinson's disease.

Pyridazinone derivatives and processes for preparing the same

Disclosed are a pyridazinone compound represented by the formula: STR1 wherein (1) R1 is a substituted or unsubstituted C1-10 alkyl, a C3-6 cycloalkyl, a lower alkenyl, a heterocyclic group having N, O or S atom or camphor-10-yl; R3 is hydrogen, a substituted or unsubstituted lower alkyl or a lower alkenyl; or R1 and R3 are bonded at terminal ends thereof to form a lower alkylene; and Z is a group represented by the formula: STR2 where n is 1 or 2; and D is hydrogen or a halogen; or (2) R1 is a substituted or unsubstituted C1-10 alkyl, a substituted or unsubstituted phenyl, a C3-6 cycloalkyl, a lower alkenyl, a heterocyclic group having N, O or S atom or camphor-10-yl; R3 is hydrogen, a substituted or unsubstituted lower alkyl or a lower alkenyl; or R1 and R3 are bonded at terminal ends thereof to form a lower alkylene; and Z is a group represented by the formula: STR3 and R2 is hydrogen, a substituted or unsubstituted lower alkyl, an aryl or a lower alkenyl; and --A--B-- is an ethylene or vinylene each of which may be substituted by 1 or 2 groups selected from the group consisting of a lower alkyl and phenyl group, or a pharmaceutically acceptable salt thereof, and processes for preparing the same.

Indane derivatives for treating endotoxin shock and/or nephritis

Disclosed are indane compounds represented by the formula: STR1 wherein R1 is aryl, lower alkyl, cycloalkyl, halogeno-lower alkyl, lower alkenyl, phenyl-substituted lower alkenyl, monocyclic or bicyclic aromatic heterocyclic having N, O or S as a hetero atom, lower alkoxy, phenoxy, lower alkylamino, lower alkenylamino, phenylamino, lower alkyl substituted by monocyclic or bicyclic aromatic heterocyclic having N, O or S as a hetero atom, or lower alkenyloxy; R2 is H or lower alkyl; X is carbonyl or thiocarbonyl; Alk is single bonding arm or lower alkylene; and the dotted line is presence or absence of a double bond, for treating endotoxin shock and/or nephritis.

DERIVATIVES OF 4-(AMINOMETHYL) PIPERIDINE, THEIR PREPARATION AND THEIR THERAPEUTIC APPLICATION

Compounds of general formula (I) STR1 in which n is 1 or 2; R represents a linear or branched C 1-C 3-alkyl group; andX represents at least one substituent chosen from hydrogen, halogen, C 1-C 3-alkyl and C 1-C 3-alkoxy, in the form of a free base or an acid addition salt thereof, and their therapeutic application.

Comparison of Biological Effects of N-Alkylated Congeners of β-Phenylethylamine Derived from 2-Aminotetralin, 2-Aminoindan, and 6-Aminobenzocycloheptene

Three series of bicyclic, semirigid congeners of β-phenethylamine have been prepared for evaluation of the effect of ring size (and of concomitant conformational variation) on biological activity in a variety of assays for adrenergic and dopaminergic actions.Pharmacologic activity was associated with 2-aminotetralin and 2-aminoindan derivatives, but was not found with 6-aminobenzocycloheptene derivatives.Noteworthy is the ability of several aminotetralins and aminoindans to increase the hot-plate reaction time without eliciting dopaminergic effects.This action was not blocked by pretreatment with naloxone.