The reaction of Digitoxin and Digoxin with cyanoacetic acid hydrazide: Synthesis of Coumarin, Thiazole, Thiophene and Pyridine derivatives with potential biological activities

2001 ◽  
Vol 24 (5) ◽  
pp. 377-384 ◽  
Author(s):  
Senot H. Doss ◽  
Wagnat W. Wardakhan ◽  
Nadia A. Louca
Keyword(s):  
Biological Activities ◽  
Acid Hydrazide ◽  
Pyridine Derivatives ◽  
Cyanoacetic Acid ◽  
Cyanoacetic Acid Hydrazide

Synthesis of Some New Tetracyclic Pyrimidine Derivatives Using Exocyclic α,β-Unsaturated Ketone and Evaluation of Their Antitumor Activities

2016 ◽  
Vol 12 (8) ◽  
pp. 311-317
Author(s):  
Kamelia El-Mahdy
Keyword(s):  
Antitumor Activity ◽  
Spectroscopic Data ◽  
Acid Hydrazide ◽  
Chloroacetic Acid ◽  
Equimolar Amount ◽  
Unsaturated Ketone ◽  
Cyanoacetic Acid ◽  
Antitumor Activities ◽  
Pyrimidine Derivatives ◽  
Cyanoacetic Acid Hydrazide

Thiazolopyrimidine 2 was obtained from the reaction of dihydropyrimidinone with chloroacetic acid and benzaldehyde. Thiazolopyrimidine 2 containing an α,β-unsaturated ketonic function [-CH=CH-CO-] has been used as a component of Michael addition with an equimolar amount of dinucleophiles to give a series of novel tetracyclic pyrimidine derivatives. Treatment of thiazolopyrimidine 2 with uracil, aminotriazole, cyanoacetic acid hydrazide, o-phenylenediamine or diaminopyridine afforded the corresponding pyridopyrimidine, triazolopyrimidine, pyrazolone, benzodiazepine and triazepine derivative, respectively. The detailed synthesis, spectroscopic data, and antitumor activity for synthesized compounds were reported.

Chelate-assisted synthesis of pyrazolylidene derivatives from cyanoacetic acid hydrazide and O-methyl lactims

2014 ◽  
Vol 63 (10) ◽  
pp. 2260-2263
Author(s):  
S. V. Ruban ◽  
T. V. Potapova ◽  
S. V. Baranin ◽  
V. A. Dorokhov
Keyword(s):  
Acid Hydrazide ◽  
Cyanoacetic Acid ◽  
Cyanoacetic Acid Hydrazide

Synthesis and reactions of indeno[1,2-c]chromene-6,11-dione derivatives

2008 ◽  
Vol 2008 (11) ◽  
pp. 609-612 ◽  
Author(s):  
Mahmoud R. Mahmoud ◽  
Manal M. El-Shahawi ◽  
Eman A.A. El-Bordany ◽  
Fatma S.M. Abu El-Azm
Keyword(s):  
Mass Spectra ◽  
Acid Hydrazide ◽  
Sodium Hydride ◽  
Hydroxylamine Hydrochloride ◽  
Cyanoacetic Acid ◽  
H Nmr ◽  
Concentrated Sulfuric Acid ◽  
Nitrogen Nucleophiles ◽  
Cyanoacetic Acid Hydrazide ◽  
C Nmr

Indeno[1,2-c]chromene-6,11-dione was prepared using the readily obtainable starting materials via the condensation of dimethyl homophthalate with 2,6-dichlorobenzaldehyde in the presence of sodium hydride in dry benzene followed by saponification and cyclisation with concentrated sulfuric acid at 0°C. The tendency of indeno[1,2-c]chromene-6,11-dione for undergoing nucleophilic addition has been tested by reaction with nitrogen nucleophiles such as hydrazine hydrate, hydroxylamine hydrochloride, ethyl carbazate, cyanoacetic acid hydrazide, thiosemicarbazide and 4-methylbenzenesulfonohydrazide. The IR, 1H NMR, 13C NMR and mass spectra of the synthesised compounds are discussed.

Synthesis of Some New 1, 3, 4-Oxadiazole, Pyrazole, and Pyrimidine Bearing Thienopyrazole Moieties

2020 ◽  
Vol 17 (8) ◽  
pp. 661-670
Author(s):  
Mohamed Ahmed Elian Sophy ◽  
Mohamed Ahmed Mahmoud Abdel Reheim
Keyword(s):  
Biological Activities ◽  
Research Work ◽  
Ethyl Cyanoacetate ◽  
Acid Hydrazide ◽  
Pharmacological Activities ◽  
Mannich Reactions ◽  
Chemical Structures ◽  
Elemental Analyses ◽  
Electrophilic Reagents ◽  
Cyanoacetic Acid Hydrazide

Aim and Objective: According to the literature survey, pyrazole is a unique template that is associated with several biological activities. This article highlighted the research work of many researchers reported in the literature for synthesis and different pharmacological activities of the pyrazole nucleus. In the present work, pyrazol- 3-one 1 was reacted with cyanoacetic acid hydrazide and elemental sulfur to afford the corresponding thieno[3,2-c]pyrazol-6-carbohydrazide 3 derivatives. The latter compound reacted with some electrophilic reagents such as DMF-DMA, triethylorthoformate, arylidenemalononitriles and chalcones under neat conditions to give substituted oxadiazole and pyrazole, respectively. The treatment of compound 3 with active methylene reagents such as acetylacetone, diethylmalonate, ethyl acetoacetate and ethyl cyanoacetate under suitable conditions afforded pyrazole derivatives 10, 11, 13, and 15, respectively. Novel pyrazolothienopyrimidine 27 and 30 were prepared from precursor 26 with carbon disulfide and triethylorthoformate, respectively. The chemical structures of the newly synthesized compounds were established by elemental and spectral analyses including IR, and 1HNMR in addition to 13C-NMR and mass spectra. Materials and Methods: A novel substituted pyrazole, pyrimidine and pyrazolothienopyrimidine were obtained via Gewald synthesis of thiophene and fused thiophene and Mannich reactions of 5-amino-3-phenyl-1Hthieno[ 3,2-c]pyrazole-6-carbohydrazide. Results and Discussion: A series of some newly azoles and azines were prepared via reaction of thieno[3,2- c]pyrazol-6-carbohydrazide derivative 3 as starting material with some electrophilic and nucleophilic reagents. The structures of target compounds were established by elemental analyses and spectral data. Conclusion: Pyrazole is a unique template that is associated with several biological activities. This article highlighted the research work of many researchers reported in the literature for synthesis and different pharmacological activities of the pyrazole nucleus. In the current investigation, we have developed new and efficient methods for the synthesis of thieno[3,2-c]pyrazol-6-carbohydrazide derivatives. In addition, we have explored the preparative potential of these substances as intermediates for the synthesis of substituted pyrazoles and fused pyrazoles 10-30, respectively.

scholarly journals Utility of Activated Nitriles in the Synthesis of Novel Heterocyclic Compounds with Antitumor Activity

2013 ◽  
Vol 2013 ◽  
pp. 1-9 ◽  
Author(s):  
Asmaa S. Salman
Keyword(s):  
Heterocyclic Compounds ◽  
Acid Hydrazide ◽  
Cancer Cell Line ◽  
Human Breast ◽  
Cyanoacetic Acid ◽  
Elemental Analyses ◽  
Cyanoacetic Acid Hydrazide ◽  
Antitumor Evaluation ◽  
Mcf 7

Reaction of cyanoacetic acid hydrazide (1) with 4-methoxyacetophenone and 4-chlorobenzaldehyde (2a,b) afforded the corresponding 2-cyanoacetohydrazide derivatives (3a,b) respectively. The latter compounds were utilized as a key intermediate for the synthesis of new heterocyclic compounds. Newly synthesized compounds were characterized by elemental analyses and spectral data. The antitumor evaluation of some newly synthesized compounds was screened in vitro against human breast cancer cell line (MCF-7).

ChemInform Abstract: A Study of Cyanoacetic Acid Hydrazide.

ChemInform ◽  
2010 ◽  
Vol 24 (6) ◽  
pp. no-no
Author(s):  
A. A. IKIZLER ◽  
A. IKIZLER ◽  
N. UZUNISMAIL
Keyword(s):  
Acid Hydrazide ◽  
Cyanoacetic Acid ◽  
Cyanoacetic Acid Hydrazide

scholarly journals Utility of cyanoacetic acid hydrazide in heterocyclic synthesis

ARKIVOC ◽  
2006 ◽  
Vol 2006 (9) ◽  
pp. 113-156 ◽  
Author(s):  
Samir Bondock ◽  
Abd El-Gaber El-Tarhoni ◽  
Ahmed A. Fadda
Keyword(s):  
Acid Hydrazide ◽  
Heterocyclic Synthesis ◽  
Cyanoacetic Acid ◽  
Cyanoacetic Acid Hydrazide

scholarly journals Synthesis of Some New Tetracyclic Pyrimidine Derivatives Using Exocyclic α,β-Unsaturated Ketone and Evaluation of Their Antitumor Activities

2008 ◽  
Vol 4 (1) ◽  
pp. 311-317
Author(s):  
Kamelia El-Mahdy
Keyword(s):  
Antitumor Activity ◽  
Spectroscopic Data ◽  
Acid Hydrazide ◽  
Chloroacetic Acid ◽  
Equimolar Amount ◽  
Unsaturated Ketone ◽  
Cyanoacetic Acid ◽  
Antitumor Activities ◽  
Pyrimidine Derivatives ◽  
Cyanoacetic Acid Hydrazide

Thiazolopyrimidine 2 was obtained from the reaction of dihydropyrimidinone with chloroacetic acid and benzaldehyde. Thiazolopyrimidine 2 containing an α,β-unsaturated ketonic function [-CH=CH-CO-] has been used as a component of Michael addition with an equimolar amount of dinucleophiles to give a series of novel tetracyclic pyrimidine derivatives. Treatment of thiazolopyrimidine 2 with uracil, aminotriazole, cyanoacetic acid hydrazide, o-phenylenediamine or diaminopyridine afforded the corresponding pyridopyrimidine, triazolopyrimidine, pyrazolone, benzodiazepine and triazepine derivative, respectively. The detailed synthesis, spectroscopic data, and antitumor activity for synthesized compounds were reported.

Synthesis and characterization of novel bis(pyridine-2(1H)-thiones) and their bis(2-methylsulfanylpyridines) incorporating 2,6-dibromophenoxy moiety

2019 ◽  
Vol 97 (1) ◽  
pp. 53-60 ◽  
Author(s):  
Sherif M.H. Sanad ◽  
Azza M. Abdel-Fattah ◽  
Fawzy A. Attaby ◽  
Mohamed A.A. Elneairy
Keyword(s):  
Acid Hydrazide ◽  
Synthesis And Characterization ◽  
The Novel ◽  
Cyanoacetic Acid ◽  
Elemental Analyses ◽  
Hydrazide Derivative ◽  
Target Molecules ◽  
Cyanoacetic Acid Hydrazide ◽  
Active Methylene

The novel 1,4-bis(2,6-dibromo-4-formylphenoxy)butane (3), prepared from 3,5-dibromobenzaldehyde (1), reacted with different hydrazines 4a–4d and active methylene containing compounds 9a–9d to give the corresponding bis(hydrazones) 5a–5d and bis(cinnamonitriles) 11a–11d, respectively. Both bis(2-cyanoacetic acid hydrazide) derivative 5d and bis(thioacrylamide) derivative 11a were taken as synthetic precursors for the synthesis of the target molecules bis(pyridine-2(1H)-thione) derivative 10 and 13a–13c and their bis(2-methylsulfanylpyridine) derivative 14 and 17a–17c. Another synthetic route was designed to prepare the target molecules 14 and 17a–17c in a better yield using pyridine-2(1H)-thione) derivative 15 and 19a–19c. Characterization of the newly prepared compounds via elemental analyses and spectral data are established.

scholarly journals Reaction of Carbon Disulfide with Cyanoacetic Acid Hydrazide: Novel Synthesis of Thiazole and Thiazolo[4,5-c]pyrazole

1999 ◽  
Vol 23 (1) ◽  
pp. 10-11
Author(s):  
Rafat M. Mohareb ◽  
Suzan I. Aziz ◽  
Nadia I. Abdel-Sayed ◽  
Ahmed H. El-Banna
Keyword(s):  
Carbon Disulfide ◽  
Acid Hydrazide ◽  
Cyanoacetic Acid ◽  
Thiazole Derivatives ◽  
Novel Synthesis ◽  
Cyanoacetic Acid Hydrazide

The reaction of cyanoacetic acid hydrazide with carbon disulfide in basic dimethylformamide afforded the potassium thiocarbamate 2 which underwent ready heterocyclization upon its reaction with α-haloketones to give the thiazole derivatives 4 and 23.

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