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At least 19 recordsLinked to original sources

PubMed2004

Synthesis and antimicrobial activities of some new 1-(5-phenylamino-[1,3,4]thiadiazol-2-yl)methyl-5-oxo-[1,2,4]triazole and 1-(4-phenyl-5-thioxo-[1,2,4]triazol-3-yl)methyl-5-oxo- [1,2,4]triazole derivatives.

Acetic acid ethyl esters containing 5-oxo-[1,2,4]triazole ring (2) were synthesized by the condensation of compounds 1a-f with ethyl bromoacetate in basic media. The reaction of compounds 2a-f with hydrazine hydrate led to the formation of acid hydrazides (3a-f). The treatment of compounds 3 with two divers aromatic aldehydes resulted in the formation of arylidene hydrazides as cis-trans conformers (4a,c,e,f, 5a,e,f). The thiosemicarbazide derivatives (6a,c,d,f) were afforded by the reaction of corresponding compounds 3 with phenylisothiocyanate. The treatment of compounds 6a,c,d,f with sulfuric acidic caused the conversion of side-chain of compounds 6a,c,d,f into 1,3,4-thiadiazol ring; thus, compounds 7a,c,d,f were obtained. On the other hand, the cyclization of compounds 6a,c,d,f in the presence of 2 N NaOH resulted in the formation of compounds 8a,c,d,f containing two [1,2,4]triazole rings which are linked to each other via a methylene bridge. Compounds 4a, f, 5a, 7a, d, f, 8a and d have shown antimicrobial activity against one or more microorganism, but no antifungal activity has been observed against yeast like fungi. Also inhibitory effect on mycelial growth by compounds 4e, 7d and 8f has been observed. Compounds 4c and 5f were found to possess antitumor active towards breast cancer.

Anti-Bacterial Agents↗

PubMed1987

[Reactivity of 3-aryl-4-amino-5-mercapto-4H-1,2,4-triazoles: synthesis and biological evaluation of 3,6-diaryl derivatives of 7H-1,2,4-thiazole[3,4-b][1,3,4]thiadiazines, of 3-aryl-4-amino-5-carboxymethylthio-4H-1,2,4-triazoles].

Starting from 3-aryl-4-amino-5-mercapto-4H-1,2,4-triazoles (II), two series of 3,6-disubstituted 7H-1,2,4-triazol [3,4-b] [1,3,4] thiadiazines (III) and their 5-carboxymethylthio derivatives (IV) were prepared. From the mercapto-amino-triazoles (II) because of their reactivity in some oxidising media, were obtained the triazole derivatives (V), (VI) and (VII). The synthesis of the alpha-thioketones (VIII) of 3-aryl-5-mercapto-1,3,4-oxadiazoles (I), used in alternative synthesis of triazole-thiadiazines (III), is also reported. All the substances described were subjected to biological screening. In the tests, the carboxymethylthiotriazole (IV) showed weak antiinflammatory activity (carrageenin edema) and more consistent scavanger activity, in vitro, on superoxide anions. The triazole-thiadiazines (III) and triazoles (II), (V) and (VI) showed moderate antimycotic activity.

Analgesics↗

PubMed1993

Nonpeptide angiotensin II antagonists derived from 4H-1,2,4-triazoles and 3H-imidazo[1,2-b][1,2,4]triazoles.

By a variety of synthetic routes, we have synthesized a series of 3,4,5-trisubstituted 4H-1,2,4-triazoles and a related series of 3H-imidazo[1,2-b][1,2,4]triazoles and evaluated them in vitro and in vivo as angiotensin II (AII) antagonists. Principal efforts focused on triazoles bearing an n-alkyl substitutent at C3 and a 4-[(2-carboxybenzoyl)amino]benzyl, (2'-carboxybiphenyl-4-yl)methyl, or [2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl side chain at N4. Among numerous variations at C5, benzylthio groups gave the best potency. Particularly noteworthy was 3-n-butyl-5-[(2-carboxybenzyl)thio]-4-[[2'-(1H-tetrazol-5-yl )biphenyl-4 - yl]methyl]-4H-1,2,4-triazole (71, IC50 1.4 nM), which blocked the AII pressor response in conscious rats at 0.3 mg/kg iv with a duration of action of approximately 6 h, similar to that of DuP 753. Although 71 was active orally only at a 10-fold higher dose level, good oral bioavailability was demonstrated for a monoacidic analogue 62. Most potent among the bicyclic derivatives was 2-n-butyl-5,6-dimethyl-3-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]meth yl]- 3H-imidazo[1,2-b][1,2,4]triazole (93, IC50 7.8 nM). The effects of hydrophobic, hydrogen-bonding, and ionic interactions with the AT1 receptor are considered.

Angiotensin II↗

PubMedDate not supplied

Studies on epimeric D-xylo-and D-lyxo-tetritol-1-yl-2-phenyl-2H-1,2,3-triazoles. Synthesis and anomeric configuration of 4-(alpha-and beta-D-threofuranosyl)-2-phenyl-2H-1,2,3-triazole C-nucleoside analogs.

Treatment of 4-(D-xylo-tetritol-1-yl)-2-phenyl-2H-1,2,3-triazole (1) with one mole equivalent of tosyl chloride in pyridine solution, afforded the C-nucleoside analog; 4-(beta-D-threofuranosyl)-2-phenyl-2H-1,2,3-triazole (2) in 55% yield, as well as the byproduct 4-(4-chloro-4-deoxy-D-xylo-tetritol-1-yl)-2-phenyl-2H-1,2,3-triazo le (4). Treatment of the epimeric 4-(D-lyxo-tetritol-1-yl)-2-phenyl-2H-1,2,3-triazole (6) with tosyl chloride in pyridine solution afforded the anomeric C-nucleoside analog; 4-(alpha-D-threofuranosyl)-2-phenyl-2H-1,2,3-triazole (7) in 29% yield, as well as the byproduct 4-(4-chloro-4-deoxy-D-lyxo-tetritol-1-yl)-2-phenyl-2H-1,2,3- triazole (9). Similar treatment of 1 and 6 with trifluoromethanesulfonyl chloride in pyridine solution afforded 2 and 7, respectively. The structure and anomeric configuration of these compounds were determined by acetylation, NMR, NOE, and circular dichroism spectroscopy, as well as mass spectrometry.

Acetylation↗

PubMed2002

Synthesis of 3-alkyl(aryl)-4-alkylidenamino-4,5-dihydro-1H-1,2,4-triazol-5-ones and 3-alkyl-4-alkylamino-4,5-dihydro-1H-1,2,4-triazol-5-ones as antitumor agents.

A series of 3-alkyl-4-phenylethylidenamino- (8) and 3-alkyl-4-(3-phenylallylidenamino)-4,5-dihydro-1H-1,2,4-triazol-5-ones (9) was synthesized from the reaction of the corresponding 3-alkyl(aryl)-4-amino-4,5-dihydro-1H-1,2,4-triazol-5-ones (1), with phenylacetaldehyde and cinnamaldehyde. 3-Alkyl-4-(2-phenylethylamino)- (10) and 3-alkyl-4-(3-phenylpropylamino)-4,5-dihydro-1H-1,2,4-triazol-5-ones (11) were obtained from the selective reduction of compounds (8) and (9) with NaBH(4). The in vitro antitumor activity of the novel compounds was screened and the highest inhibition of tree tumor cell lines was observed for the compounds containing phenylethylenamino and phenylethylamino groups at position 4 of 1,2,4-triazol ring.

Antineoplastic Agents↗

PubMed1988

Structures of the anticancer compounds N-(2-hydroxyethyl)-2-(3-nitro-1,2,4-triazol-1-yl)-acetamide (RB-6110) and 5-(1-aziridinyl)-3-nitro-1-(3-oxo-1-butyl)-1,2,4- triazole (RB-6162).

RB-6110: C6H9N5O4, Mr = 215.17, monoclinic, C2/c, a = 20.595 (3), b = 4.713 (1), c = 19.914 (4) A, beta = 110.69 (1) degree, V = 1808.3 A3, Z = 8, Dx = 1.588 Mg m-3, lambda(Cu K alpha) = 1.54178 A, mu = 0.838 mm-1, F(000) = 675, T = 298 K, final R = 0.042 for 1219 observed reflections with I greater than or equal to 1.5 sigma (I). RB-6162: C8H11N5O3, Mr = 225.21, monoclinic, P2(1)/c, a = 7.515 (1), b = 14.758 (2), c = 9.813 (1) A, beta = 108.49 (1) degree, V = 1032.1 A3, Z = 4, Dx = 1.450 Mg m-3, lambda(Cu K alpha) = 1.54178 A, mu = 0.927 mm-1, F(000) = 472, T = 298 K, final R = 0.042 for 1113 observed reflections with I greater than or equal to 1.5 sigma (I). RB-6110 and RB-6162 are 3-nitro-1,2,4-triazoles with potential application as anticancer agents. The nitro groups are in the plane of the aromatic triazole ring with dihedral angles of 1.2 (4) and 4.6 (4) degrees, respectively. The arizidine substituent of RB-6162 is almost perpendicular [dihedral angle 80.1 (4) degrees] to the triazole plane. Molecular-orbital calculations on RB-6162 have confirmed that this geometry is energetically favoured. The energy barrier to rotation about the triazole-aziridine bond has been determined as 51.5 (5) kJ mol-1 by the dynamic NMR method.

Antineoplastic Agents↗

PubMed1992

s-triazole systems. Part IV: Novel substituted thio-s-triazole derivatives.

Interaction of (3-aryloxymethyl-4-phenyl-s-triazol-5-yl)thioacethydrazid e (1a-c) with phenyl isocyanate and/or with methyl/phenyl isothiocyanate gave semicarbazides (2a-c) and thiosemicarbazides (3a-f) respectively. Cyclization of (3a-f) yielded s-triazoles (4a-f). Compounds 4b,d,f were easily alkylated giving S-substituted thio-s-triazoles (5a-e). Furthermore, compounds 4b,d,f underwent a Mannich reaction to give the expected Mannich bases (6a-f). All compounds were fully confirmed by elemental and spectral analyses and have been screened in vitro for antimicrobial activity.

Anti-Bacterial Agents↗

PubMedDate not supplied

Novel synthesis of seco type of acyclo C-nucleosides of 1,2,4-triazole and 1,2,4-triazol.

The seco C-nucleosides 3-(1,2,3,4,5-penta-O-acetyl-D-gluco- and D-galacto-pentitol-1-yl)-1H-1,2,4-triazoles (8 and 9) were obtained in a one pot by deamination and dethiolation of 4-amino-3-(D-gluco- and D-galacto-pentitol-1-yl)-5-mercapto-1,2,4-triazoles (1 and 2), respectively, using sodium nitrite in orthophosphoric acid and subsequent acetylation. Condensation of 1, 2, and 4-amino-3-(D-glycero-D-gulo-hexitol-1-yl)-5-mercapto-1,2,4-triazole (12) with phenacylbromide (11) afforded the corresponding 3-(D-gluco-, D-galactopentitol-1-yl) and 3-(D-glycero-D-gulo-hexitol-1-yl)-6-phenyl-7H-1,2,4-triazolo[3,4-b][1,3,4] thiadiazines (15, 16, and 17). Acetylation of 15-17 gave the penta- and hexa-O-acetyl derivatives 18-20, respectively. The structures were confirmed by using 1H, 13C, and 2D NMR spectra, DQFCOSY, HMQC, and HMBC experiments. The favored conformational structures were deduced from the vicinal coupling constants of the protons.

Acetylation↗

PubMed2005

4,4'-Butane-1,4-diylbis[3-ethyl-1H-1,2,4-triazol-5(4H)-one] and 4-hydroxy-3-n-propyl-1H-1,2,4-triazol-5(4H)-one.

The title compounds, C12H20N6O2, (I), and C5H9N3O2, (II), display the characteristic features of 1,2,4-triazole derivatives. Compound (I) lies about an inversion centre which is at the mid-point of the central C-C bond. Compound (II) also contains a planar 1,2,4-triazole ring but differs from (I) in that it has a hydroxy group attached to the ring. Molecules of (I) are held together in the crystal structure by intermolecular N-H...O contacts and by weak pi-pi stacking interactions between the 1,2,4-triazole moieties. Compound (II) contains intermolecular O-H...O and N-H...O hydrogen bonds.

Butanes↗

PubMedDate not supplied

Synthesis of new 1-(amino)-3-[(1,5-diphenyl-1H-1,2,4-triazol-3-yl) oxy] propan-2-ol and 1-[(1,5-diphenyl- 1H- 1,2,4-triazol-3-yl) oxy]-3-(4-arylpiperazin-1-yl) propan-2-ol derivatives with an expected beta-adrenolytic activity.

3-(Oxiran-2-ylmethoxy)-l ,5-diphenyl-lH-1,2,4-triazole [I] was obtained in the reaction of 1,5-di-phenyl-IH-1,2,4-triazol-3-ol with 2-(chloromethyl) oxirane. Then I was converted into the corresponding aminoalkanol derivatives of 1,5-diphenyl-IH-1,2,4-triazol-3-ol, IIa,b -VIIa,b. Molecular structure of I was confirmed by an X- ray structure analysis. The receptor affinities for IVa, VIIa were determined.

Adrenergic beta-Antagonists↗

PubMed1995

Xanthine oxidase (XO). 4(5)-aminosubstituted-5(4)-carboxyamido-1H-1,2, 3-triazoles: a new class of monocyclic triazole inhibitors.

The 4(5)-aminosubstituted-5(4)-carboxyamido-1H-1,2,3-triazoles constitute a new class of monocyclic compounds as effective inhibitors of XO. In the past to these compounds the structure of 9-unsubstituted-8-azahypoxanthines was wrongly attributed. However some 8-azahypoxanthines obtained via a new annulation reaction have been described in this paper. The inhibitory activity of the title triazoles resulted greater than that shown by the corresponding 8-azahypoxanthines. The inhibitory competitive activity of 4(5)-n-pentyloxyoxalylamino-5(4)-carbamoyl-1H-1,2,3-triazole toward the oxidation of 8-n-pentylhypoxanthine disclosed that only one lipophilic pocket is present within the enzyme.

Molecular Structure↗

PubMed2002

Cyclic trinuclear and chain of cyclic trinuclear copper(II) complexes containing a pyramidal Cu(3)O(H) core. Crystal structures and magnetic properties of [Cu(3)(mu(3)-OH)(aaat)(3)(H(2)O)(3)](NO(3))(2).H(2)O [aaat = 3-acetylamino-5-amino-1,2,4-triazolate] and ([Cu(3)(mu(3)-OH)(aat)(3)(mu(3)-SO(4))].6H(2)O)(n) [aat = 3-acetylamino-1,2,4-triazolate]: new cases of spin-frustrated systems.

New copper(II) complexes of the cyclic trinuclear type with 1,2,4-triazole ligands, [Cu(3)(mu(3)-OH)(aaat)(3)(H(2)O)(3)](NO(3))(2).H(2)O [Haaat = 3-acetylamino-5-amino-1,2,4-triazole] (1) and ([Cu(3)(mu(3)-OH)(aat)(3)(mu(3)-SO(4))].6H(2)O)(n) [Haat = 3-acetylamino-1,2,4-triazole] (2), have been prepared and characterized by X-ray crystallography and magnetic measurements. Compound 1, the first reported with the ligand (H)aaat, consists of discrete trinuclear cations, associated NO(3)(-) anions and lattice water molecules. Compound 2 consists of unusual chains of trinuclear units with a tridentate sulfato group linking the trimeric units and water molecules stabilizing the crystal lattice. In both complexes, 1 and 2, the trinuclear [Cu(3)(OH)L(3)] unit contains a pyramidal Cu(3)-mu(3)OH core, and an almost flat Cu(3)N(6) ring formed by the N,N-bridging triazolato groups. The Cu...Cu' intratrimeric distances are 3.35-3.37-3.39 A in 1 and 3.34-3.34-3.36 A in 2. The copper atoms are five-coordinated with a distorted square-pyramidal geometry. Magnetic measurements have been performed in the 1.9-300 K temperature range. In the high-temperature region (T > 90 K), experimental data could be satisfactorily reproduced by using an isotropic exchange model, H = -J(S(1)S(2) + S(2)S(3) + S(1)S(3)), with J = -194.6 cm(-1) and g = 2.08 for 1, and J = -185.1 cm(-1) and g = 2.10 for 2. The magnitude of the antiferromagnetic exchange in both complexes is discussed on the basis of their structural features by comparison with reported N,N-pheripherically bridged trinuclear systems. In order to fit the experimental magnetic data at low temperature, an antisymmetric exchange term, H(AS) = G(S(1)xS(2) + S(2)xS(3) + S(1)xS(3)), had to be introduced, with G = 27.8 (1) and 31.0 (2) cm(-1). Crystal data: C(12)H(27)Cu(3)N(17)O(14) (1) (MW = 824.13) crystallizes in the triclinic space group, P(-)1, Z = 2, with the cell dimensions a = 8.852(2) A, b = 11.491(3) A, c = 15.404(3) A, alpha = 70.43(3) degrees, beta = 75.11(2) degrees, gamma = 88.43(2) degrees, and V = 1423.8(5) A(3), D(calcd) = 1.922 g cm(-)(3); the final agreement values were R1 = 0.0822 and wR2 = 0.2300 for 4989 unique reflections. C(12)H(28)Cu(3)N(12)O(14)S (2) (MW = 787.14) crystallizes in the triclinic space group, P(-)1, Z = 2, with the cell dimensions a = 7.146(6) A, b = 14.26(1) A, c = 15.35(2) A, alpha = 109.0(9) degrees, beta = 93.6(9) degrees, gamma = 99.5(7) degrees, and V = 1448(2) A(3), D(calcd) = 1.806 g cm(-3); the final agreement values were R1 = 0.0628 and wR2 = 0.1571 for 3997 "observed" reflections.

Journal Article↗

PubMed1983

Studies on v-triazoles. 7. Antiallergic 9-oxo-1H,9H-benzopyrano[2,3-d]-v-triazoles.

A series of the little compounds was prepared by cyclization of the appropriate 5-(aryloxy)-v-triazole-4-carboxylic acids and evaluated for antiallergic activity by the rat passive cutaneous anaphylaxis (PCA) screen. The most potent compounds were 6-(mesyloxy)-9-oxo-1H,9H-benzopyrano[2,3-d]-v-triazole and its 5-methyl homologue, which were some tenfold more potent than disodium cromoglycate. Dialkyl derivatives, especially those substituted at C-5 and C-6 or C-6 and C-7, and 6-methoxy compounds were also among the more potent compounds. One compound, 6,7-dimethyl-9-oxo-1H,9H-benzopyrano[2,3-d]-v-triazole, was further evaluated and shown to be a potent inhibitor of rat PCA when given orally.

Animals↗

PubMed2005

Tetrakis(1-ethyl-1H-1,2,4-triazole-kappaN4)bis(nitrato-kappaO)copper(II) and bis(nitrato-kappaO)tetrakis(1-propyl-1H-1,2,4-triazole-kappaN4)copper(II).

The copper(II) environments for tetrakis(1-ethyl-1,2,4-triazole)dinitratocopper(II), [Cu(NO3)2(C4H7N3)4], and tetrakis(1-propyl-1,2,4-triazole)dinitratocopper(II), [Cu(NO3)2(C5H9N3)4], are distorted square bipyramidal. Both structures are centrosymmetric, with the copper(II) ions located at inversion centers coordinated by four N atoms of four triazole molecules and by two O atoms of two nitrate ions in an elongated octahedral geometry. This elongation is a result of the Jahn-Teller effect. The largest distortion is that of the N-Cu-O angles, which differ from 90 degrees by 5.68 (10) degrees in the ethyl and 5.59 (8) degrees in the propyl derivative.

Journal Article↗

PubMed2006

N-H...N and C-H...pi interactions in 4-amino-3-methyl-5-(p-tolyl)-4H-1,2,4-triazole and 4-amino-3-methyl-5-phenyl-4H-1,2,4-triazole.

The title compounds, C10H12N4, (I), and C9H10N4, (II), have been synthesized and characterized both spectroscopically and structurally. The dihedral angles between the triazole and benzene ring planes are 26.59 (9) and 42.34 (2) degrees, respectively. In (I), molecules are linked principally by N-H...N hydrogen bonds involving the amino NH2 group and a triazole N atom, forming R(4)4(20) and R(2)4(10) rings which link to give a three-dimensional network of molecules. The hydrogen bonding is supported by two different C-H...pi interactions from the tolyl ring to either a triazole ring or a tolyl ring in neighboring molecules. In (II), intermolecular hydrogen bonds and C-H...pi interactions produce R(3)4(15) and R(4)4(21) rings.

Journal Article↗

PubMed1990

Synthesis and anti-human immunodeficiency virus (HIV-1) activity of 3'-deoxy-3'-(triazol-1-yl)thymidines and 2',3'-dideoxy-3'-(triazol-1-yl)uridines and inhibition of reverse transcriptase by their 5'-triphosphates.

3'-Deoxy-3'-(1,2,3-triazol-1-yl)thymidines (5a, 6a, 8a, 11a, and 12a) and 2',3'-dideoxy-3'-(1,2,3-triazol-1-yl)uridines (5b, 6b, 8b, 11b, and 12b) were synthesized as cyclic analogues of 3'-azido-3'-deoxythymidine (AZT) and 3'-azido-2',3'-dideoxyuridine (CS-87) by the cyclization of 5'-trityl derivatives (1a, b) of AZT and CS-87 using alpha-ketophosphorus ylides and with acetylenic compounds followed by deprotection of the 5'-trityl group. It was hypothesized that the triazole nitrogen atoms could mimic and distorted azido group. However, no significant activity against human immunodeficiency virus type 1 (HIV-1) was observed with any of these compounds. 5'-Triphosphates (17a and 18a, b), prepared from 5a and 6a, b, were inactive against HIV-1 and Rauscher murine leukemia virus (RLV) reverse transcriptases.

Acquired Immunodeficiency Syndrome↗

PubMed1985

Potential antihypertensives. Synthesis of 6-substituted-N-(4H-1,2,4-triazol-4-yl)-3-pyridazinamines and 3-substituted-6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)pyridazines.

A series of 6-substituted-N-(4H-1,2,4-triazol-4-yl)-3-pyridazinamines [(II), Scheme 1] and 3-substituted-6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl) pyridazines [(XII), Scheme 3-5] were synthesized. The compounds were evaluated for their oral antihypertensive activity in rats (SHR) and only some compounds of structure (XII) induced a moderate decrease in systolic blood pressure.

Animals↗

PubMed1986

Studies on 1,2,3-triazoles. 13. (Piperazinylalkoxy) [1]benzopyrano[2,3-d]-1,2,3-triazol-9(1H)-ones with combined H1-antihistamine and mast cell stabilizing properties.

Several N-benzylpiperazino derivatives of [1]benzopyrano[2,3-d]-1,2,3-triazol-9(1H)-one and its 5-methyl homologue have been prepared and evaluated for H1-antihistamine activity on guinea pig ileum. The most potent compounds were also evaluated for their ability to stabilize mast cells in the rat passive peritoneal anaphylaxis (PPA) system and were shown to inhibit histamine release at concentrations below those required to inhibit extravasation, suggesting that this might be relevant to their antianaphylactic activity in this system. The compound tested with the most potent H1-antihistamine activity was 6-[3-[4-(4-chlorobenzyl)-1-piperazinyl]propoxy][1]benzopyrano[2,3- d]-1,2,3-triazol-9(1H)-one, 28, which had a pA2 of 9.1 against histamine on guinea pig ileum, comparable to that of mepyramine, and inhibited histamine release in the rat PPA system with an IC50 value of 5.4 X 10(-6) M.

Anaphylaxis↗