Derivatives of 2-Amino-1,2,3,4-Tetrahydronaphthalene,X. Syntheses of N-Alkyl- and -Dialkylaminoalkanoyl Derivatives of trans-2-Amino-3-hydroxy-5,8-dimethoxy-1,2,3,4-tetrahydro-naphthalene

By reacting trans-2-amino-3-hydroxy-5,8-dimethoxytetraline (1) with chloroacetyl chloride, the amide 2 was obtained. With primary and secondary amines 2 gives the N-alkyl- and N-dialkylaminoacetyl derivatives 3a-i. Compound 3c possesses antiarrhythmic activity.     

Derivatives of 2-amino-1,2,3,4-tetrahydronaphthalene. XI: trans-6,9-dimethoxy-2,3,4a,5,10,10a-hexahydro-4H-naphth[2,3-b]1, 4-oxazines--tricyclic analogs trans-2-amino-3-hydroxy-5,8-dimethoxytetralins

Cyclization of chloroacetyl derivatives of the aminotetraloles 2 and 3 in alcoholic KOH yields 3-oxonaphthalane-morpholines. Their reduction with LiAlH₄ gave the naphthalane-morpholines 5 . The pharmacological screening of 5a ′ showed central stimulative, peripheral adrenergic, and analgetic activities.     

Derivate des 2-Amino-1,2,3,4-Tetrahydronaphthalins,II. Synthese und pharmakologische Untersuchung von N-substituierten trans-2-Amino-3-hydroxy-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalinen

Derivatives of 2-Amino-1,2,3,4-Tetrahydronaphthalene, II: Synthesis and Pharmacological Investigation of N-Substituted trans-2-Amino-3-hydroxy-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalenes By epoxydation of 5,8-dimethoxy-1,4-dihydronaphthalene the epoxide I was obtained. Reactions with certain aminoalcohols and primary or secondary amines led to the N-substituted derivatives of trans-2-amino-3-hydroxy-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalene 1--14 . On pharmacological testing the hydrochlorides of the new compounds showed significant biological activity.     

Derivate des 2-Amino-1,2,3,4-tetrahydronaphthalins, 7. Mitt. Aroylester des cis- und trans-2-Dimethylamino-3-hydroxy-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalins

Derivatives of 2-Amino-1,2,3,4-tetrahydronaphthalene, VII: Aroyl Esters of cis- and trans-2-Dimethylamino-3-hydroxy-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalenes By acylation of cis- and trans-2-dimethylamino-3-hydroxy-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalene (2) with the chlorides of some aromatic acids, the aroyl esters 1 were obtained. The new compounds show spasmolytic and local anesthetic activities.     

Derivate des 2-Amino-1,2,3,4-tetrahydronaphthalins, 6. Mitt. IR-Spektroskopische Konformationsermittlung einiger 2-Amino-3-hydroxy-5,8-dimethoxy-1,2,3,4-tetrahydronaphthaline

Derivatives of 2-Amino-1,2,3,4-tetrahydronaphthalene, VI: IR-Spectroscopic Determination of the Conformational Equilibrium of Some 2-Amino-3-hydroxy-1,2,3,4-tetrahydronaphthalenes. The conformational characteristics of cis- and trans-2-amino-3-hydroxy-5,8-dimethoxytetralins and some N-substituted derivatives were investigated by analysing their IR spectra. A high degree of hydrogen bonding for the trans compounds and a preferred diequatorial conformation were established. The spectra of the cis isomers show the presence of a larger population of the rotamer with axial OH group. The scheme for the synthesis of cis-AT is presented.     

Derivatives of 2-amino-1,2,3,4-tetrahydronaphthalene. I. Synthesis of some N-substituted trans-2-amino-3-hydroxy-1,2,3,4-tetrahydronaphthalenes (author's transl)

Derivatives of 2-Amino-3-hydroxy-1,2,3,4-tetrahydronaphthalene. I. Synthesis of Some N-Substituted trans-2-Amino-3-hydroxy-1,2,3,4-tetrahydronaphthalenes By addition of some aminoalcohols, aminophenols, amino acids and cyclic amines 2,3-epoxytetralin, ten new N-substituted trans-2-amino-3-hydroxy-1,2,3,4-tetrahydronaphthalenes (1–10) are obtained. The heating of the ethyleneimine base 9 leads to its dimer 11 . The configuration of these compounds is discussed.     

Derivatives of 2-amino-1,2,3,4-tetrahydronaphthalene, IX: Structure-activity relationships of cis- and trans-2-amino-5,8-dimethoxytetralin-3-ols and some analogues

The structure-activity relationships of cis- and trans-2-amino-5,8-dimethoxytetralin-3-ols and some of their analogues are discussed. A correlation was established between the stereochemical characteristics of the compounds and their pharmacological effects.     

Antiproliferative Activity of 3-Cyanocoumarins and 2-Aminochromeno[2,3-b ]Pyridine-3-Carbonitriles,Derivatives of 2-Amino-4H-Chromene-3-Carbonitrile

Pharmaceutical Chemistry Journal - The antiproliferative activity of the previously synthesized 2-amino-4H-chromene-3-carbonitrile derivatives 4,7-disubstituted 3-cyanocoumarins and...     

Investigations on the synthesis and pharmacological properties of amides of 7-methyl-3-phenyl-1-[2-hydroxy-3-(4-phenyl-1-piperazinyl)propyl]-2,4- dioxo-1,2,3,4-tetrahydropyrido[2,3-d]-pyrimidine-5-carboxylic acid

Synthesis of amides of 7-methyl-3-phenyl-2,4-dioxo-1,2,3,4- tetrahydropyrido[2,3-d]pyrimidine-5-carboxylic acid (6-10) and their 1-[2-hydroxy-3(4-phenyl-1-piperazinyl)propyl] derivatives (11-15) are described. Some of them displayed strong analgesic activity.     

Synthesis and pharmacological properties of N,N-dialkyl(dialkenyl)amides of 7-methyl-3-phenyl-1-[2-hydroxy-3-(4-phenyl-1-piperazinyl)propyl]-2,4-dioxo-1,2,3,4-tetrahydropyrido[2,3-d]pyrimidine-5-carboxylic acid

Synthesis of N,N-dialkyl(dialkenyl)amides of 7-methyl-3-phenyl-2,4-dioxo-1,2,3,4-tetrahydropyrido[2,3-d]pyrimidine-5-carboxylic acid (5-9) and their 1-[2-hydroxy-3-(4-phenyl-1-piperazinyl)propyl] derivatives (10-14) is described. Compounds 10-14 were tested for analgesic and sedative activities as well as for mu-opioid receptors binding affinities. All the amides, being the object of investigation, displayed an interesting analgesic action, which in case of the compounds 10-12 and 14 was superior to that of acetylsalicylic acid in two different tests. Furthermore all the amides (10-14) significantly suppressed the spontaneous locomotor activity, prolonged barbiturate sleep in mice and showed a weak affinity to mu-opioid receptors.     

Synthesis and properties of amides of 1-benzyl-3-methyl- and 1-butyl-3-phenyl-7-methyl-4-oxo-2-thioxo (2,4-dioxo)-1,2,3,4-tetrahydropyrido-[2,3-d]pyrimidine-6-carboxy lic acids

Amides of 1-benzyl-3,7-dimethyl-4-oxo-2-thioxo-1,2,3,4- tetrahydropyrido[2,3]pyrimidine-6-carboxylic acid were obtained by the condensation of ammonia, primary and secondary cyclic amines with the corresponding acid chloride. As by - products amides of 1-benzyl-3,7-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrido[2,3-d]pyr imidine-6- carboxylic acid were isolated as a result of desulfuration. The same reaction performed with chloride of 1-butyl-7-methyl-3-phenyl-4-oxo-2-thioxo-1,2,3,4-tetrahydropyri do[2,3- d]pyrimidine-6-carboxylic acid gave mainly the corresponding 2,4-dioxo-amides.     

Synthesis and pharmacological properties of 1-[2-hydroxy-3-(4-o,m,p-halogenophenyl)- and 3-(4-m-chlorophenyl)-1-piperazinyl]propyl derivatives of amides of 7-methyl-3-phenyl-2,4-dioxo-1,2,3,4-tetrahydropyrido [2,3-d]pyrimidine-5-carboxylic acid with analgesic and sedative activities

Synthesis of 1-[2-hydroxy-3-(4-o,m,p-halogenophenyl)- and 3-(4-m-chlorophenyl)-1-piperazinyl]propyl derivatives of amides of 7-methyl-3-phenyl-2,4-dioxo-1,2,3,4-tetrahydropyrido[2,3-d]pyrimidine-5-carboxylic acid (18, 20-23, 25, 27-30 and 19, 24, 26) is described. All substances were active as analgesic agents in writhing syndrome test and except of 18 and 23 they acted stronger than acetylsalicylic acid. All final derivatives tested significantly suppressed the spontaneous locomotor activity of mice.     

Design,Synthesis, Docking and Antitumor Activity of Quinazolino [3, 4-a] thieno [3, 2-d] pyrimidin-8-one Derivatives

Several novel quinazolino [3, 4-a] thieno [3, 2-d] pyrimidin-8-one derivatives were synthesized. All of the compounds were determined against MiaPaCa2 and DU145 cells in vitro, and the crystal structures of analog 8 and 20 in the active site of the EGFR complexes were presented. The entire compounds had been identified by ¹HNMR, ¹³CNMR, IR, MS and EA.     

Synthesis of new pyrido[4',3':4,5]thieno[2,3-d]-1,2,4-triazolo[3,4-c]pyrimidines and a 5,6-dihydro-1,2,4-triazolo[4",3":1',2']pyrido[4',3':4,5]thieno [2,3-d]-pyrimidine ring system

A series of substituted pyrido[4',3':4,5]thieno[2,3-d]-1,2,4-triazolo[3,4-c]pyrimidines 4-6, 8, pyrido[4',3':4,5]thieno[2,3-d]-1,2,4-triazolo[3,4-c]pyrimidines 11-13 and 5,6-dihydro-1,2,4-triazolo[4",3":1',2']pyrido[4',3':4,5]thieno[2,3-d] pyrimidines 16-19 have been synthesized from 3, 10 and 15 through the reaction with orthoesters and carbon disulphide, respectively.