Home Nitros 1H-Imidazole-1-acetamide, 2-nitro-N-(phenylmethyl)-

1H-Imidazole-1-acetamide, 2-nitro-N-(phenylmethyl)-

CAS No.:
22994-85-0
Catalog Number:
AG002LSW
Molecular Formula:
C12H12N4O3
Molecular Weight:
260.2487
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Purity
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Location
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Product Description
Catalog Number:
AG002LSW
Chemical Name:
1H-Imidazole-1-acetamide, 2-nitro-N-(phenylmethyl)-
CAS Number:
22994-85-0
Molecular Formula:
C12H12N4O3
Molecular Weight:
260.2487
MDL Number:
MFCD00243089
IUPAC Name:
N-benzyl-2-(2-nitroimidazol-1-yl)acetamide
InChI:
InChI=1S/C12H12N4O3/c17-11(14-8-10-4-2-1-3-5-10)9-15-7-6-13-12(15)16(18)19/h1-7H,8-9H2,(H,14,17)
InChI Key:
CULUWZNBISUWAS-UHFFFAOYSA-N
SMILES:
O=C(Cn1ccnc1[N+](=O)[O-])NCc1ccccc1
UNII:
YC42NRJ1ZD
NSC Number:
299972
Properties
Complexity:
325  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
260.091g/mol
Formal Charge:
0
Heavy Atom Count:
19  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
1  
Isotope Atom Count:
0
Molecular Weight:
260.253g/mol
Monoisotopic Mass:
260.091g/mol
Rotatable Bond Count:
4  
Topological Polar Surface Area:
92.7A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
0.9  
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Molecular modeling studies and in vitro bioactivity evaluation of a set of novel 5-nitro-heterocyclic derivatives as anti-T. cruzi agents. Bioorganic & medicinal chemistry 20090401
A systematic review of studies on heart transplantation for patients with end-stage Chagas' heart disease. Journal of cardiac failure 20090401
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Identification of three classes of heteroaromatic compounds with activity against intracellular Trypanosoma cruzi by chemical library screening. PLoS neglected tropical diseases 20090201
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Evaluation of high efficiency gene knockout strategies for Trypanosoma cruzi. BMC microbiology 20090101
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Etiological treatment of young women infected with Trypanosoma cruzi, and prevention of congenital transmission. Revista da Sociedade Brasileira de Medicina Tropical 20090101
Genotoxicity revaluation of three commercial nitroheterocyclic drugs: nifurtimox, benznidazole, and metronidazole. Journal of parasitology research 20090101
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Beneficial effects of benznidazole during an infectious-based situation of systemic inflammatory response: cecal ligation and puncture. The American journal of tropical medicine and hygiene 20081101
Anti-T. cruzi agents: our experience in the evaluation of more than five hundred compounds. Mini reviews in medicinal chemistry 20081101
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Chagas disease and the US blood supply. Current opinion in infectious diseases 20081001
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Benznidazole biotransformation in rat heart microsomal fraction without observable ultrastructural alterations: comparison to Nifurtimox-induced cardiac effects. Memorias do Instituto Oswaldo Cruz 20080901
Naphthoquinoidal [1,2,3]-triazole, a new structural moiety active against Trypanosoma cruzi. European journal of medicinal chemistry 20080801
Pyrimido[1,2-a]quinoxaline 6-oxide and phenazine 5,10-dioxide derivatives and related compounds as growth inhibitors of Trypanosoma cruzi. European journal of medicinal chemistry 20080801
Complexation of the anti-Trypanosoma cruzi drug benznidazole improves solubility and efficacy. Journal of medicinal chemistry 20080724
New trypanocidal hybrid compounds from the association of hydrazone moieties and benzofuroxan heterocycle. Bioorganic & medicinal chemistry 20080715
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Proteomic analysis of Trypanosoma cruzi resistance to Benznidazole. Journal of proteome research 20080601
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Synthesis and anti-Trypanosoma cruzi activity of derivatives from nor-lapachones and lapachones. Bioorganic & medicinal chemistry 20080501
Drug-induced cure drives conversion to a stable and protective CD8+ T central memory response in chronic Chagas disease. Nature medicine 20080501
Synthesis of a small library of 2-phenoxy-1,4-naphthoquinone and 2-phenoxy-1,4-anthraquinone derivatives bearing anti-trypanosomal and anti-leishmanial activity. Bioorganic & medicinal chemistry letters 20080401
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Changes of RAPD profile of Trypanosoma cruzi II with Canova and Benznidazole. Homeopathy : the journal of the Faculty of Homeopathy 20080401
Acute chagasic myocardiopathy after orthotopic liver transplantation with donor and recipient serologically negative for Trypanosoma cruzi: a case report. Transplantation proceedings 20080401
Efficient inhibition of iron superoxide dismutase and of Trypanosoma cruzi growth by benzo[g]phthalazine derivatives functionalized with one or two imidazole rings. Journal of medicinal chemistry 20080327
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Natural chromenes and chromene derivatives as potential anti-trypanosomal agents. Biological & pharmaceutical bulletin 20080301
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Trypanosoma cruzi: activities of lapachol and alpha- and beta-lapachone derivatives against epimastigote and trypomastigote forms. Bioorganic & medicinal chemistry 20080115
Synthesis and antiprotozoal activities of simplified analogs of naphthylisoquinoline alkaloids. European journal of medicinal chemistry 20080101
Trypanosoma cruzi: characterisation of the gene encoding tyrosine aminotransferase in benznidazole-resistant and susceptible populations. Experimental parasitology 20080101
Leishmanicidal and trypanocidal activities of 2-aminocyclohexanol and 1,2-cyclohexanediamine derivatives. Bioorganic & medicinal chemistry letters 20080101
Sterol 14-demethylase inhibitors for Trypanosoma cruzi infections. Advances in experimental medicine and biology 20080101
Trypanosomiasis vector control in Africa and Latin America. Parasites & vectors 20080101
Trypanosoma cruzi alkaline 2-DE: Optimization and application to comparative proteome analysis of flagellate life stages. Proteome science 20080101
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Silencing cytokeratin 18 gene inhibits intracellular replication of Trypanosoma cruzi in HeLa cells but not binding and invasion of trypanosomes. BMC cell biology 20080101
Synthesis and in vitro evaluation of leishmanicidal and trypanocidal activities of N-quinolin-8-yl-arylsulfonamides. Bioorganic & medicinal chemistry 20071215
Targeted screening strategies to detect Trypanosoma cruzi infection in children. PLoS neglected tropical diseases 20071201
Combining residual insecticide spraying campaigns with targeted detection and specific chemotherapy for Trypanosoma cruzi infection in children. PLoS neglected tropical diseases 20071201
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In vivo anti-Chagas vinylthio-, vinylsulfinyl-, and vinylsulfonylbenzofuroxan derivatives. Journal of medicinal chemistry 20071129
Synthesis and evaluation of antiparasitic activities of new 4-[5-(4-phenoxyphenyl)-2H-pyrazol-3-yl]morpholine derivatives. Journal of medicinal chemistry 20071115
Marine natural products from the Turkish sponge Agelas oroides that inhibit the enoyl reductases from Plasmodium falciparum, Mycobacterium tuberculosis and Escherichia coli. Bioorganic & medicinal chemistry 20071101
An overview of Chagas disease treatment. Memorias do Instituto Oswaldo Cruz 20071030
Allopurinol is effective to modify the evolution of Trypanosoma cruzi infection in mice. Parasitology research 20071001
Early nifurtimox-induced biochemical and ultrastructural alterations in rat heart. Human & experimental toxicology 20071001
Synthesis, Cruzain docking, and in vitro studies of aryl-4-oxothiazolylhydrazones against Trypanosoma cruzi. ChemMedChem 20070901
Synthesis and in vitro protozoocidal activity of diazabicyclic benzotropolone derivatives. Bioorganic & medicinal chemistry letters 20070801
Chagas disease: clinical overview and implications for nursing. Medsurg nursing : official journal of the Academy of Medical-Surgical Nurses 20070801
DNA damage and nitric oxide synthesis in experimentally infected Balb/c mice with Trypanosoma cruzi. Experimental parasitology 20070701
Treatment with benznidazole or thioridazine in the chronic phase of experimental Chagas disease improves cardiopathy. International journal of antimicrobial agents 20070601
Usefulness of PCR strategies for early diagnosis of Chagas' disease reactivation and treatment follow-up in heart transplantation. American journal of transplantation : official journal of the American Society of Transplantation and the American Society of Transplant Surgeons 20070601
Chagas' disease reactivation with skin symptoms in a patient with kidney transplant. International journal of dermatology 20070601
Mode of action of natural and synthetic drugs against Trypanosoma cruzi and their interaction with the mammalian host. Comparative biochemistry and physiology. Part A, Molecular & integrative physiology 20070401
The Anti-Trypanosoma cruzi activity of posaconazole in a murine model of acute Chagas' disease is less dependent on gamma interferon than that of benznidazole. Antimicrobial agents and chemotherapy 20070401
Second generation of 5-ethenylbenzofuroxan derivatives as inhibitors of Trypanosoma cruzi growth: synthesis, biological evaluation, and structure-activity relationships. Bioorganic & medicinal chemistry 20070401
In vitro and in vivo trypanocidal activity of the ethyl esters of N-allyl and N-propyl oxamates using different Trypanosoma cruzi strains. Journal of enzyme inhibition and medicinal chemistry 20070401
In vitro and in vivo activity of lignan lactones derivatives against Trypanosoma cruzi. Parasitology research 20070301
Liver transplantation from deceased donors serologically positive for Chagas disease. American journal of transplantation : official journal of the American Society of Transplantation and the American Society of Transplant Surgeons 20070301
1,4-Bis(alkylamino)benzo[g]phthalazines able to form dinuclear complexes of Cu(II) which as free ligands behave as SOD inhibitors and show efficient in vitro activity against Trypanosoma cruzi. Bioorganic & medicinal chemistry 20070301
[Chest pain and peripheral eosinophilia]. Revista clinica espanola 20070201
Effects of canthin-6-one alkaloids from Zanthoxylum chiloperone on Trypanosoma cruzi-infected mice. Journal of ethnopharmacology 20070119
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Synthesis, in vitro evaluation, and SAR studies of a potential antichagasic 1H-pyrazolo[3,4-b]pyridine series. Bioorganic & medicinal chemistry 20070101
Manifestations of Chagas disease (American trypanosomiasis) in patients with HIV/AIDS. Annals of tropical medicine and parasitology 20070101
Trypanocide treatment among adults with chronic Chagas disease living in Santa Fe city (Argentina), over a mean follow-up of 21 years: parasitological, serological and clinical evolution. Revista da Sociedade Brasileira de Medicina Tropical 20070101
Novel potential drug against T. cruzi and its interaction with surfactant micelles. Pharmaceutical development and technology 20070101
Chagas disease: an impediment in achieving the Millennium Development Goals in Latin America. BMC international health and human rights 20070101
Mexican Trypanosoma cruzi isolates: in vitro susceptibility of epimastigotes to anti-trypanosoma cruzi drugs and metacyclic forms to complement-mediated lysis. Vector borne and zoonotic diseases (Larchmont, N.Y.) 20070101
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An insight on targets and patented drugs for chemotherapy of Chagas disease. Recent patents on anti-infective drug discovery 20070101
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Synthesis and trypanocidal activity of 1,4-bis-(3,4,5-trimethoxy-phenyl)-1,4-butanediol and 1,4-bis-(3,4-dimethoxyphenyl)-1,4-butanediol. Bioorganic & medicinal chemistry 20061101
Benznidazole treatment during early-indeterminate Chagas' disease shifted the cytokine expression by innate and adaptive immunity cells toward a type 1-modulated immune profile. Scandinavian journal of immunology 20061101
In vitro antiprotozoal activity of the lipophilic extracts of different parts of Turkish Pistacia vera L. Phytomedicine : international journal of phytotherapy and phytopharmacology 20061101
Increased expression of iron-containing superoxide dismutase-A (TcFeSOD-A) enzyme in Trypanosoma cruzi population with in vitro-induced resistance to benznidazole. Acta tropica 20061101
Activity of neolignans isolated from Piper regnellii (MIQ.) C. DC. var. pallescens (C. DC.) YUNCK against Trypanosoma cruzi. Biological & pharmaceutical bulletin 20061001
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Polymerase chain reaction detection and serologic follow-up after treatment with benznidazole in Bolivian children infected with a natural mixture of Trypanosoma cruzi I and II. The American journal of tropical medicine and hygiene 20060901
Improving anti-trypanosomal activity of 3-aminoquinoxaline-2-carbonitrile N1,N4-dioxide derivatives by complexation with vanadium. Bioorganic & medicinal chemistry 20060815
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Design, synthesis and evaluation of novel uracil amino acid conjugates for the inhibition of Trypanosoma cruzi dUTPase. Bioorganic & medicinal chemistry letters 20060715
Development of resazurin microtiter assay for drug sensibility testing of Trypanosoma cruzi epimastigotes. Parasitology research 20060701
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The thymus is a common target organ in infectious diseases. PLoS pathogens 20060601
Summaries for patients. Long-term outcomes of treating nonacute Chagas disease with benznidazole. Annals of internal medicine 20060516
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Microsphere-based protease assays and screening application for lethal factor and factor Xa. Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501
Chagas disease: hidden affliction and visible neglect. CMAJ : Canadian Medical Association journal = journal de l'Association medicale canadienne 20060411
Deletion of copies of the gene encoding old yellow enzyme (TcOYE), a NAD(P)H flavin oxidoreductase, associates with in vitro-induced benznidazole resistance in Trypanosoma cruzi. Molecular and biochemical parasitology 20060401
Treatment of experimental chronic chagas disease with trifluralin. Basic & clinical pharmacology & toxicology 20060401
Development of parenteral formulations and evaluation of the biological activity of the trypanocide drug benznidazole. International journal of pharmaceutics 20060113
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[Recommendations for diagnosis, treatment and follow-up of the Trypanosoma cruzi: human immunodeficiency virus co-infection]. Revista da Sociedade Brasileira de Medicina Tropical 20060101
Molecular diagnosis and typing of Trypanosoma cruzi populations and lineages in cerebral Chagas disease in a patient with AIDS. The American journal of tropical medicine and hygiene 20051201
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Isoneocryptolepine, a synthetic indoloquinoline alkaloid, as an antiplasmodial lead compound. Journal of natural products 20050501
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Benznidazole-induced genotoxicity in diploid cells of Aspergillus nidulans. Memorias do Instituto Oswaldo Cruz 20050501
Trypanocidal activity of N-isopropyl oxamate on cultured epimastigotes and murine trypanosomiasis using different Trypanosoma cruzi strains. Journal of enzyme inhibition and medicinal chemistry 20050401
Benznidazole vs benznidazole in multilamellar liposomes: how different they interact with blood components? Memorias do Instituto Oswaldo Cruz 20050401
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The trypanocidal effect of sesquiterpene lactones helenalin and mexicanin on cultured epimastigotes. The Journal of parasitology 20050201
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Benznidazole, a drug used in Chagas' disease, ameliorates LPS-induced inflammatory response in mice. Life sciences 20041224
Ancistrobenomine a, the first naphthylisoquinoline oxygenated at Me-3, and related 5,1'-coupled alkaloids, from the 'new' plant species ancistrocladusbenomensis. Journal of natural products 20041201
Trypanosoma cruzi: inhibition of alpha-hydroxyacid dehydrogenase isozyme II by N-allyl and N-propyl oxamates and their effects on intact epimastigotes. Memorias do Instituto Oswaldo Cruz 20041201
Short report: benznidazole efficacy among Trypanosoma cruzi-infected adolescents after a six-year follow-up. The American journal of tropical medicine and hygiene 20041101
Intravenous liposomal benznidazole as trypanocidal agent: increasing drug delivery to liver is not enough. International journal of pharmaceutics 20040708
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Ancistrotanzanine C and related 5,1'- and 7,3'-coupled naphthylisoquinoline alkaloids from Ancistrocladus tanzaniensis. Journal of natural products 20040501
Chagas seropositive donors in kidney transplantation. Transplantation proceedings 20040501
In vitro activity of Etanidazole against the protozoan parasite Trypanosoma cruzi. Memorias do Instituto Oswaldo Cruz 20040301
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Effects of buthionine sulfoximine nifurtimox and benznidazole upon trypanothione and metallothionein proteins in Trypanosoma cruzi. Biological research 20040101
[Longitudinal study and specific chemotherapy in children with chronic Chagas' disease, residing in a low endemicity area of Argentina]. Revista da Sociedade Brasileira de Medicina Tropical 20040101
Lack of correlation between in vitro susceptibility to Benznidazole and phylogenetic diversity of Trypanosoma cruzi, the agent of Chagas disease. Experimental parasitology 20040101
Benznidazole-induced ultrastructural and biochemical alterations in rat esophagus. Toxicology 20030930
Synthesis and evaluation of a series of 1,4-diarylbutadienes for anticoccidial activity. Bioorganic & medicinal chemistry 20030901
Enzyme-linked immunoassay using recombinant trans-sialidase of Trypanosoma cruzi can be employed for monitoring of patients with Chagas' disease after drug treatment. Clinical and diagnostic laboratory immunology 20030901
Ancistrotanzanine A, the first 5,3'-coupled naphthylisoquinoline alkaloid, and two further, 5,8'-linked related compounds from the newly described species Ancistrocladus tanzaniensis. Journal of natural products 20030901
Liposomal benznidazole: a high-performance liquid chromatographic determination for biodistribution studies. Journal of chromatographic science 20030901
Trypanosoma cruzi: genetic group with peculiar biochemical and biological behavior. Memorias do Instituto Oswaldo Cruz 20030701
The activity of diguanidino and 'reversed' diamidino 2,5-diarylfurans versus Trypanosoma cruzi and Leishmania donovani. Bioorganic & medicinal chemistry letters 20030616
Synthesis and in vitro trypanocide activity of several polycyclic drimane-quinone derivatives. Bioorganic & medicinal chemistry 20030612
Nitroheterocyclic drugs with broad spectrum activity. Parasitology research 20030601
Inhibition of Trypanosoma cruzi alpha-hydroxyacid dehydrogenase-isozyme II by N-isopropyl oxamate and its effect on intact epimastigotes. Journal of enzyme inhibition and medicinal chemistry 20030601
Synthesis and biological evaluation of pyrazolylnaphthoquinones as new potential antiprotozoal and cytotoxic agents. Chembiochem : a European journal of chemical biology 20030103
[Anti-F2/3 antibodies as cure marker in children with congenital Trypanosoma cruzi infection]. Medicina 20030101
Trypanosoma cruzi: susceptibility to chemotherapy with benznidazole of clones isolated from the highly resistant Colombian strain. Revista da Sociedade Brasileira de Medicina Tropical 20030101
Treatment with benznidazole in association with immunosuppressive drugs in mice chronically infected with Trypanosoma cruzi: investigation into the possible development of neoplasias. Revista da Sociedade Brasileira de Medicina Tropical 20030101
[Trypanosoma cruzi high parasitemia in patient with systemic lupus erythematosus]. Revista da Sociedade Brasileira de Medicina Tropical 20030101
Synthesis and in vitro anti-protozoal activity of a series of benzotropolone derivatives incorporating endocyclic hydrazines. European journal of medicinal chemistry 20030101
Development and in vitro characterisation of a benznidazole liposomal formulation. International journal of pharmaceutics 20021205
Relationship between long-term resistance to Trypanosoma cruzi and latent infection, examined by antibody production and polymerase chain reaction in mice. The Journal of parasitology 20021201
Biological characterization of a beta-galactosidase expressing clone of Trypanosoma cruzi CL strain. Memorias do Instituto Oswaldo Cruz 20021201
Chemotherapy of Chagas' disease: status and new developments. Current topics in medicinal chemistry 20021101
Proinflammatory and cytotoxic effects of hexadecylphosphocholine (miltefosine) against drug-resistant strains of Trypanosoma cruzi. Antimicrobial agents and chemotherapy 20021101
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Experimental chemotherapy against Trypanosoma cruzi infection: essential role of endogenous interferon-gamma in mediating parasitologic cure. The Journal of infectious diseases 20020915
Cerebral trypanosomiasis and AIDS. Arquivos de neuro-psiquiatria 20020901
Ancistrocongolines A-D, new naphthylisoquinoline alkaloids from ancistrocladus congolensis. Journal of natural products 20020801
Voltammetric behavior of benznidazole at a DNA-electrochemical biosensor. Journal of pharmaceutical and biomedical analysis 20020701
Trypanosoma cruzi trypanothione reductase inhibitors: phenothiazines and related compounds modify experimental Chagas' disease evolution. Current drug targets. Cardiovascular & haematological disorders 20020601
The restoring effect of trifluralin and benznidazole on the abnormal fatty-acid pattern induced by Trypanosoma cruzi in the liver microsomes of infected mice. Annals of tropical medicine and parasitology 20020401
In vitro and in vivo assays of 3,5-disubstituted-tetrahydro-2H-1,3,5-thiadiazin-2-thione derivatives against Trypanosoma cruzi. Memorias do Instituto Oswaldo Cruz 20020301
African trypanosomiasis in travelers returning to the United Kingdom. Emerging infectious diseases 20020101
Trypanocidal drugs for chronic asymptomatic Trypanosoma cruzi infection. The Cochrane database of systematic reviews 20020101
Long term evaluation of etiological treatment of chagas disease with benznidazole. Revista do Instituto de Medicina Tropical de Sao Paulo 20020101
A critical review on Chagas disease chemotherapy. Memorias do Instituto Oswaldo Cruz 20020101
TNF-alpha is expressed at sites of parasite and tissue destruction in the spleen of mice acutely infected with Trypanosoma cruzi. International journal of experimental pathology 20011201
Experimental treatment of chronic Trypanosoma cruzi infection in mice with 2-n-propylquinoline. Phytotherapy research : PTR 20011101
Anti-Trypanosoma activity of some natural stilbenoids and synthetic related heterocyclic compounds. Bioorganic & medicinal chemistry letters 20011022
Drug resistance in Trypanosoma cruzi is not associated with amplification or overexpression of P-glycoprotein (PGP) genes. Molecular and biochemical parasitology 20011001
Variation in susceptibility to benznidazole in isolates derived from Trypanosoma cruzi parental strains. Memorias do Instituto Oswaldo Cruz 20011001
Trypanocidal drug benznidazole impairs lipopolysaccharide induction of macrophage nitric oxide synthase gene transcription through inhibition of NF-kappaB activation. Journal of immunology (Baltimore, Md. : 1950) 20010915
Design, synthesis, and biological evaluation of a series of simple and novel potential antimalarial compounds. Bioorganic & medicinal chemistry letters 20010723
Treatment with benznidazole and its immunomodulating effects on Trypanosoma cruzi-infected rats. Parasitology research 20010701
Adenosine analogues as selective inhibitors of glyceraldehyde-3-phosphate dehydrogenase of Trypanosomatidae via structure-based drug design. Journal of medicinal chemistry 20010621
Bisphosphonates inhibit the growth of Trypanosoma brucei, Trypanosoma cruzi, Leishmania donovani, Toxoplasma gondii, and Plasmodium falciparum: a potential route to chemotherapy. Journal of medicinal chemistry 20010315
A disubstituted NAD+ analogue is a nanomolar inhibitor of trypanosomal glyceraldehyde-3-phosphate dehydrogenase. Bioorganic & medicinal chemistry letters 20010122
Biological characterization of Trypanosoma cruzi strains. Memorias do Instituto Oswaldo Cruz 20010101
New thiadiazine derivatives with activity against Trypanosoma cruzi amastigotes. Folia parasitologica 20010101
Time-dependent oxidative stress caused by benznidazole. Redox report : communications in free radical research 20010101
Trypanocidal activity of 4 isopropyl salicylaldehyde and 4-isopropyl salicylic acid on Trypanosoma cruzi. Revista latinoamericana de microbiologia 20010101
Treatment of experimental pneumocystosis: review of 7 years of experience and development of a new system for classifying antimicrobial drugs. Antimicrobial agents and chemotherapy 19920901
Structure/activity relationships for the enhancement by electron-affinic drugs of the anti-tumour effect of CCNU. British journal of cancer 19820801
Enhancement by electron-affinic agents of the therapeutic effects of cytotoxic agents against the KHT tumor: structure-activity relationships. International journal of radiation oncology, biology, physics 19820101
Single-dose pharmacokinetics of the trypanosomicide benznidazole in man. Arzneimittel-Forschung 19790101
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