Design, synthesis and biological activity of novel non-peptidyl endothelin converting enzyme inhibitors, 1-phenyl-tetrazole-formazan analogues

Yamazaki, Kazuto; Hasegawa, Hirohiko; Umekawa, Kayo; Ueki, Yoshitaka; Ohashi, Naohito; Kanaoka, Masaharu

doi:10.1016/s0960-894x(02)00149-x

Cited by 20 publications

(18 citation statements)

References 9 publications

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“…26 The reaction of compound 1 with hydrazine hydrate gave, quantitatively, the desired hydrazine derivative 2 which has been synthesised previously with modifications, but not completely characterised. [27][28][29] On the other hand, 5-bromo-2,4-dichloro-6-methylpyrimidine 3 was prepared through the reaction of thiourea and ethyl acetoacetate in a four-stage method. 30 The treatment of compound 2 with the latter in a mixture of NaOH in DMF at 0 ºC afforded 5-bromo-2-chloro-4-methyl-6-[2-(1phenyl-1H-tetrazol-5-yl)hydrazinyl]pyrimidine 4 (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Some Derivatives of Pyrimido[5,4-e]Tetrazolo[5,1-c][1,2,4]triazine; a Novel Heterocyclic System

Noorolahian

Shiri

2015

Journal of Chemical Research

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Several new derivatives of pyrimido [5,4-e]tetrazolo [5,1-c][1,2,4]triazine have been synthesised through the reaction of 5-hydrazinyl-1Htetrazole with 5-bromo-2,4-dichloro-6-methylpyrimidine in CHCl 3 solution at ambient conditions. Further treatment of the synthesised compound with secondary amines gave the corresponding substituted heterocycles which were subsequently cyclised into pyrimido [5,4-e] tetrazolo [5,1-c][1,2,4]triazines as derivatives of a novel heterocyclic system on treatment with NaNH 2 in CH 3 CN.

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Section: Resultsmentioning

confidence: 99%

Synthesis of Some Derivatives of Pyrimido[5,4-e]Tetrazolo[5,1-c][1,2,4]triazine; a Novel Heterocyclic System

Noorolahian

Shiri

2015

Journal of Chemical Research

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“…SANK 71894, (IC 50 = 1.0–3.2 μM) [91], able to cause blood vessel contraction and for this reason applied in hypertension, cardiovascular, and renal diseases [92]. …”

Section: Marine Bacteriamentioning

confidence: 99%

Marine Sponges and Bacteria as Challenging Sources of Enzyme Inhibitors for Pharmacological Applications

et al. 2017

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Enzymes play key roles in different cellular processes, for example, in signal transduction, cell differentiation and proliferation, metabolic processes, DNA damage repair, apoptosis, and response to stress. A deregulation of enzymes has been considered one of the first causes of several diseases, including cancers. In the last several years, enzyme inhibitors, being good candidates as drugs in the pathogenic processes, have received an increasing amount of attention for their potential application in pharmacology. The marine environment is considered a challenging source of enzyme inhibitors for pharmacological applications. In this review, we report on secondary metabolites with enzyme inhibitory activity, focusing our attention on marine sponges and bacteria as promising sources. In the case of sponges, we only reported the kinase inhibitors, because this class was the most representative isolated so far from these marine organisms.

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“…Sumitomo also have cyclic compounds [107], amino derivatives [108], thiourea derivatives [109] and hydrazone derivatives [110] (Figure 4), which inhibit ECE in micromolar concentrations. In anaesthetised rats, intraperitoneal administration of one of the 1-phenyl-tetrazole-formazan analogues was shown to reduce the pressor response to big ET-1 [51].…”

Section: Sumitomo/sumitomo Seiyaku Kkmentioning

confidence: 99%

Endothelin-converting enzyme inhibitors and their potential for cardiovascular and renal therapeutics

Doggrell¹

2004

Expert Opinion on Therapeutic Patents

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Inhibition of endothelin-converting enzyme (ECE) will reduce the levels of endothelin-1 (ET-1). A pathological effect for ECE/ET-1 on the human cardiovascular system has been suggested in systemic hypertension, pulmonary hypertension, chronic heart failure, myocardial infarction, atherosclerosis and restenosis. On the kidney, ECE/ET-1 may have a pathological role in acute and chronic renal failure, IgA nephropathy, cyclosporin toxicity, chronic renal allograft rejection and autosomal-dominant polycystic kidney disease. ECE-1 inhibitors have therapeutic potential in all of these cardiovascular and renal conditions. Selective non-peptide ECE inhibitors that have been patented include FR-901533, PD-069185, CGS-35066, SM-19712, CGS-30084 and Ro0677447. Studies with animal disease models suggest that ECE inhibitors may have a role in the treatment of pulmonary hypertension, myocardial infarction, cardiac hypertrophy and failure, restenosis and acute renal failure. There are four isoforms of ECE-1 with similar catalytic activity but differences in tissue and cellular localisation. The development of selective inhibitors of the ECE-1 isoforms may give better targeting of function/disease than the presently available ECE inhibitors.

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Design, synthesis and biological activity of novel non-peptidyl endothelin converting enzyme inhibitors, 1-phenyl-tetrazole-formazan analogues

Cited by 20 publications

References 9 publications

Synthesis of Some Derivatives of Pyrimido[5,4-e]Tetrazolo[5,1-c][1,2,4]triazine; a Novel Heterocyclic System

Synthesis of Some Derivatives of Pyrimido[5,4-e]Tetrazolo[5,1-c][1,2,4]triazine; a Novel Heterocyclic System

Marine Sponges and Bacteria as Challenging Sources of Enzyme Inhibitors for Pharmacological Applications

Endothelin-converting enzyme inhibitors and their potential for cardiovascular and renal therapeutics

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