[1-(2,5-Dichloroanilino)-5-methyl-1H-1,2,3-triazol-4-yl]methanol

In the title compound, C10H10Cl2N4O, the hy­droxy group and benzene ring are disposed to opposite sides of the central 1,2,3-triazolyl ring. The dihedral angle between the five- and six-membered rings is 87.51 (12)°, and the C-O bond of the hy­droxy group lies almost normal to the plane of the 5-membered ring [N-C-C-O = -93.2 (2)°]. An intra­molecular amino-N-H...Cl hydrogen bond is noted. In the extended structure, supra­molecular layers in the ab plane are formed via hy­droxy-O-H...N(ring) and amine-N-H...O(hy­droxy) hydrogen bonds. The layers are connected along the c axis by [pi]-[pi] contacts between benzene rings [inter-centroid distance = 3.7789 (13) Å] and by C-Cl...[pi] inter­actions

Synthetic indole and melatonin derivatives exhibit antimalarial activity on the cell cycle of the human malaria parasite Plasmodium falciparum

Discovering the mechanisms by which cell signaling controls the cell cycle of the human malaria parasite Plasmodium falciparum is fundamental to designing more effective antimalarials. To better understand the impacts of melatonin structure and function on the cell cycle of P. falciparum, we have synthesized two families of structurally-related melatonin compounds (7–11 and 12–16). All synthesized melatonin analogs were assayed in P. falciparum culture and their antimalarial activities were measured by flow cytometry. We have found that the chemical modification of the carboxamide group attached at C-3 position of the indole ring of melatonin (6) was crucial for the action of the indole-related compounds on the P. falciparum cell cycle. Among the melatonin derivatives, only the compounds 12, 13 and 14 were capable of inhibiting the P. falciparum growth in low micromolar IC50. These results open good perspectives for the development of new drugs with novel mechanisms of action

Synthesis and anti-HSV-1 activity of new 1,2,3-triazole derivatives

AbstractIn this work, a new series of arysulfonylhydrazine-1H-1,2,3-triazole derivatives were synthesized, and their ability to inhibit the in vitro replication of HSV-1 was evaluated. Among the 1,2,3-triazole derivatives, 1-[(5″-methyl-1″-(4‴-fluorophenylamino)-1H-1,2,3-triazol-4″-yl)carbonyl]-2-(4′-methylphenylsulfonyl)hydrazine and 1-[(5′-methyl-1′-(2″,5″-dichlorophenylamino)-1H-1,2,3-triazol-4′-yl)carbonyl]-2-(phenylsulfonyl)hydrazine, with IC50 values of 1.30 and 1.26μM, respectively, displayed potent activity against HSV-1. Because these compounds have low cytotoxicity, their selectivity indices are high. Under the assay conditions, they have better performance than does the reference compound acyclovir. The structures of all of the compounds were confirmed by one- and two-dimensional NMR techniques (1H, 13C-APT, COSY-1H×1H and HETCOR 1JCH) and by elemental analysis

1-Anilino-5-methyl-1H-1,2,3-triazole-4-carbaldehyde

The title compound, C10H10N4O, is twisted about the Nring—Namine bond with the dihedral angle between the 1,2,3-triazolyl and N-bound phenyl rings being 79.14 (9)°. The C-bound aldehyde group is coplanar with the triazolyl ring, with the N—C—C—O torsion angle being 3.5 (3)°. While coplanar, the aldehyde O atom is orientated in the opposite direction to the triazolyl-bound methyl group. The most prominent feature of the molecular packing is the formation of zigzag chains (glide symmetry) along the b axis and mediated by amine-N—H...N(triazolyl) hydrogen bonds. The chains are connected into supramolecular layers by phenyl- and methyl-C—H...O(aldehyde) interactions, with phenyl groups projecting to either side. Layers stack along the c axis with no directional interactions between them

Synthesis of new 2-aminocarbohydrate-1,4-naphthoquinone derivatives promoted by ultrasonic irradiation

In this report we describe the ultrasound-accelerated synthesis of new naphthoquinone derivatives 6a-f and 7a-c, which possess an aminocarbohydrate chain at the C-2 position of the quinone ring. This novel type of 1,4-naphthoquinone derivative has been synthesized under mild conditions by the reaction of 1,4-naphthoquinone (8a) or methoxylapachol (8b) with different aminocarbohydrates 9a-d. Characterization of all substances was confirmed by one- and two-dimensional nuclear magnetic resonance (NMR) techniques (¹H, 13C-APT, cosy-¹H vs. ¹H and HETCOR ¹J CH) and by high-resolution electrospray ionization mass spectrometry (HR ESI MS)

Tempol, a superoxide dismutase-mimetic drug, prevents chronic ischemic renal injury in two-kidney, one-clip hypertensive rats

Tempol, a superoxide dismutase-mimetic drug, has been shown to attenuate radical-induced damage, exerting beneficial effects in the animal models of oxidative stress and hypertension. This study evaluated the effect of Tempol on renal structural and functional alterations in two-Kidney, one-Clip hypertensive rats. In this study, young male Wistar rats had the left kidney clipped (2K1C), and sham-operated animals (Sham) were used as controls. Animals received Tempol (1mmol/L in drinking water) or vehicle for 5 weeks. Systolic blood pressure was evaluated once a week. At the end of the experimental protocol, the animals were placed in metabolic cages to collect urine (24h) and then anesthetized with thiopental (70mg/kg i.p.) to collect blood by puncturing the descending aorta for biochemical analysis, and the clipped kidney for morphological and immunohistochemical analyses. The vasodilator effect of Tempol was evaluated in mesenteric arterial bed (MAB) isolated from adult Wistar rats. The chronic treatment with Tempol prevented the development of hypertension and the increased plasma levels of urea, creatinine, and 8-isoprostane in 2K1C animals. Tempol also improved both glomeruli number and kidney volume to normal levels in the 2K1C+Tempol group. In addition, the treatment prevented the increased collagen deposition and immunostaining for renin, caspase-3, and 8-isoprostane in the stenotic kidney of 2K1C animals. Moreover, Tempol induced a dose-dependent vasodilator response in MAB from Wistar rats. These results suggest that Tempol protects the stenotic kidney against chronic ischemic renal injury and prevents renal dysfunction in the 2K1C model, probably through its antioxidant, vasodilator and antihypertensive actions