Orbital - Vol. 9 No. 4 - July - September 2017
SHORT COMMUNICATIONS

Synthesis, Characterization, Crystal Structure and Antimalarial Activity of (2E)-2-(1-{4-[(7-chloroquinolin-4-yl)amino]phenyl} ethylidene)hydrazine Carbothioamide

Yonathan de J. Parra
Escuela de Ingeniería Ambiental, Facultad de Ingeniería en Geología, Minas, Petróleos y Ambiental; Universidad Central del Ecuador, Quito 872-A, Ecuador
Rosa Elena Ferrer
Departamento de Química, Facultad de Humanidades y Educación, Universidad del Zulia
Julia Bruno-Colmenarez
Centro de Investigación y Tecnología de Materiales (CITeMa), Instituto Venezolano de Investigaciones Científicas
Jaime Charris
Laboratorio de Síntesis Orgánica, Facultad de Farmacia, Universidad Central de Venezuela
Gricela Lobo
Laboratorio de Síntesis Orgánica, Facultad de Farmacia, Universidad Central de Venezuela
Neira Gamboa de Domínguez
Laboratorio de Bioquímica, Facultad de Farmacia, Universidad Central de Venezuela
Philip J. Rosenthal
Department of Medicine, San Francisco General Hospital, University of California, San Francisco
Jiri Gut
Department of Medicine, San Francisco General Hospital, University of California, San Francisco
Published October 2, 2017
Keywords
  • thiosemicarbazones,
  • antimalarial activity,
  • crystal structure
How to Cite
(1)
Parra, Y. de J.; Ferrer, R. E.; Bruno-Colmenarez, J.; Charris, J.; Lobo, G.; de Domínguez, N. G.; Rosenthal, P. J.; Gut, J. Synthesis, Characterization, Crystal Structure and Antimalarial Activity of (2E)-2-(1-{4-[(7-Chloroquinolin-4-yl)amino]phenyl} ethylidene)hydrazine Carbothioamide. Orbital: Electron. J. Chem. 2017, 9, 308-314.

Abstract

A simple synthesis and study by UV-vis, IR, NMR, ESI-CID-MS2 and X-ray diffraction of ((2E)-2-(1-{4-[(7-chloroquinolin-4-yl)amino]phenyl}ethylidene)hydrazinecarbothioamide is reported. It was tested in vitro against chloroquine-resistant strain (W2) of Plasmodium falciparum, hemozoin (β-hematin) formation and cysteine protease falcipain-2. In general, it was found to possess a proved activity in its inhibitory power on the parasite but less active on the formation of hemozoin (β-hematin) and falcipain-2. Also, the X-ray analysis presented an unexpected electronic density that can be assigned like S(2). This electronic density can be attributed to autocondensation of thiosemicarbazide, generating H2S as a subproduct.

DOI: http://dx.doi.org/10.17807/orbital.v9i4.1001