ChemInform Abstract: Synthesis and Antihypertensive Activity of S‐Substituted 3‐Amino‐4‐(2,6‐dichlorobenzylideneamino)‐4H‐1,2,4‐triazoles and the Corresponding 3,4‐Diamino‐4H‐1,2,4‐triazoles.

Emilsson, H.; Luthman, Kristina; Selander, Hans

doi:10.1002/chin.198642180

Cited by 8 publications

(11 citation statements)

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“…They represent very convenient building blocks for preparation of various pharmaceutical substances and compounds possessing biological activity. [23][24][25][26] However, as far as we know the crystal structure of heterocyclic 1,2-diamines remains almost unknown in contrast to heterocyclic monoamines 27,28 and aliphatic 1,2diamines. 29 Meanwhile these molecules represent an interesting class of organic compounds for investigating polymorphism because they are potentially able to form different polymorphic modifications due to the different numbers of proton donating and withdrawal fragments.…”

Section: Introductionmentioning

confidence: 99%

Analysis of the crystal structure of two polymorphic modifications of 3,4-diamino-1,2,4-triazole based on the energy of the intermolecular interactions

et al. 2010

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Section: Introductionmentioning

confidence: 99%

Analysis of the crystal structure of two polymorphic modifications of 3,4-diamino-1,2,4-triazole based on the energy of the intermolecular interactions

et al. 2010

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“…Initially, due to the stronger nucleophilicity of the amino group at position 4 of the five-member ring in contrast to the amino group at position 3, [39,40] it is reasonable to assume that imine intermediate 5 is formed by condensation of 5-aryl-4H-1,2,4-triazole-3,4-diamine 1 with aldehyde 3. Then, the nucleophilic addition of isocyanide 2 to this intermediate results in formation of intermediate 6, which undergoes the intramolecular cyclization of amino group with triple bond followed by tautomerization and aerobic oxidation affords the N-alkyl-3,6-diaryl- [1,2,4]triazolo [4,3-b] [1,2,4]triazin-7-amines 4 (Scheme 2).…”

Section: Resultsmentioning

confidence: 99%

Efficient three-component synthesis of N-alkyl-3,6-diaryl-[1,2,4]triazolo[4,3-b][1,2,4]triazin-7-amines under solvent-free condition

Azimi¹,

Soheilizad²,

Zonouzi³

et al. 2017

Arkivoc

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“…AG was obtained from Dow Chemical. ALT 462 (4-amino-3-hydrazino-5-isopropyl-4H-1,2,4-triazole dihydrochloride) and ALT 486 (3,5-diamino-4-hydroxy-benzoic acid dihydrochloride) were synthesized according to the procedures previously described (25,26) (Fig. 1).…”

Section: Methodsmentioning

confidence: 99%

Chronic Dosing With Aminoguanidine and Novel Advanced Glycosylation End Product-Formation Inhibitors Ameliorates Cross-Linking of Tail Tendon Collagen in STZ-Induced Diabetic Rats

Kochakian¹,

Manjula²,

Egan³

1996

Diabetes

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Solubility of tail tendon collagen from normal, streptozotocin-induced diabetic Lewis rats, and diabetic animals treated with aminoguanidine and two novel advanced glycosylation end products (AGE)-formation inhibitors was investigated by limited pepsin digestion under acidic conditions. Assays were conducted using tail tendon collagen from Lewis rats obtained from two different vendors, Harlan and Charles River Laboratories. Collagen solubility was assessed by following the kinetics of pepsin digestion. The data revealed that the rate of digestion for diabetic animals is markedly slow relative to that of normals. More strikingly, the kinetics of the diabetic animals showed the feature of a lag in digestion regardless of the animal source. Experiments designed to optimize the difference in solubility between normal and diabetic animals demonstrated that Charles River animals exhibit a greater window of solubility than the Harlan animals. More importantly, a pronounced effect of aminoguanidine, an AGE-formation inhibitor, was observed in Charles River animals, but not in the Harlan animals, presumably because of the larger window of solubility between the normal and the diabetic animals in the former. These data indicated that the Charles River Lewis rats are an animal model that demonstrates greater efficacy in this assay. Analysis of in vivo screens designed to test efficacy of aminoguanidine and two novel AGE-formation inhibitors, ALT 462 and ALT 486, demonstrated that monitoring an in vivo dose response is highly dependent on the enzyme concentration as well as the time of digestion, and that 1.5 h of digestion and 10 microg/ml pepsin (5 pg pepsin/mg collagen) appeared optimal. Under these conditions, a 29% normalization of solubility was observed with aminoguanidine at 100 mg/kg body wt, whereas a similar normalization was observed at 10 mg/kg body wt for both ALT 462 and ALT 486. Thus, on a molar basis, ALT 462 and ALT 486 are at least 20 times more potent than aminoguanidine. This is the first demonstration of dose-dependent efficacy for AGE-formation inhibitors in animal models, and as such, this assay provides a method with which to assess the in vivo efficacy of other such inhibitors.

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ChemInform Abstract: Synthesis and Antihypertensive Activity of S‐Substituted 3‐Amino‐4‐(2,6‐dichlorobenzylideneamino)‐4H‐1,2,4‐triazoles and the Corresponding 3,4‐Diamino‐4H‐1,2,4‐triazoles.

Abstract: Triazoles of type (I)‐(III) are synthesized according to common procedures and compared with the antihypertensive agents clonidine (IV), nebidrazine (V), H 152/43 (VI) and hydralazine (VII).

Cited by 8 publications

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Analysis of the crystal structure of two polymorphic modifications of 3,4-diamino-1,2,4-triazole based on the energy of the intermolecular interactions

Analysis of the crystal structure of two polymorphic modifications of 3,4-diamino-1,2,4-triazole based on the energy of the intermolecular interactions

Efficient three-component synthesis of N-alkyl-3,6-diaryl-[1,2,4]triazolo[4,3-b][1,2,4]triazin-7-amines under solvent-free condition

Chronic Dosing With Aminoguanidine and Novel Advanced Glycosylation End Product-Formation Inhibitors Ameliorates Cross-Linking of Tail Tendon Collagen in STZ-Induced Diabetic Rats

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