Cyanoacetohydrazide - CAS 140-87-4
Catalog number:
140-87-4
Category:
Inhibitor
Not Intended for Therapeutic Use. For research use only.
Molecular Formula:
C3H5N3O
Molecular Weight:
99.09
COA:
Inquire
Targets:
Antibacterial
Description:
Cyanoacetohydrazide, a cyanoaceto compound, could be used in the treatment of tuberculosis.
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Purity:
98%
Appearance:
Powder
Synonyms:
CYANOACETYLHYDRAZINE;CYANOACETIC ACID HYDRAZIDE;CYANOACETOHYDRAZIDE;CYANOACETIC HYDRAZIDE;CYACETACIDE;LABOTEST-BB LT01121537;2-CYANOACETOHYDRAZIDE;2-CYANOETHANOHYDRAZIDE
Solubility:
DMSO: ≥ 1.2 mg/mL
Storage:
-20ºC Freeze
MSDS:
Inquire
Application:
Cyanoacetohydrazide could be used in the treatment of tuberculosis.
Shelf Life:
As supplied, 2 years from the QC date provided on the Certificate of Analysis, when stored properly
Quantity:
Grams-Kilos
Density:
1.222 g/cm3
InChIKey:
HPHBOJANXDKUQD-UHFFFAOYSA-N
InChI:
InChI=1S/C3H5N3O/c4-2-1-3(7)6-5/h1,5H2,(H,6,7)
Canonical SMILES:
C(C#N)C(=O)NN
1.Synthesis and anti-inflammatory evaluation of new substituted 1-(3-chlorophenyl)-3-(4-methoxyphenyl)-1H-pyrazole derivatives.
Fahmy HH1, Khalifa NM, Nossier ES, Abdalla MM, Ismai MM. Acta Pol Pharm. 2012 May-Jun;69(3):411-21.
A series of heterocyclic derivatives including 1,2,4-triazole-3(4H)-one (3a,b), 1H-pyrazol-5(4H)-one (4,5), 1H-pyrazol-4-carbonitrile (7), pyridine-3-carbonitrile (8, 9a,b), pyrimidine-5-carbonitrile (10a,b), methylpyrimidin-2(1H)-one or thione (11a,b), pyrimidine-5-carboxylate (12a,b), quinazolin-5(6H)-one (13a,b) and indeno [1,2-d] pyrimidin-5-one (14a,b) moieties conjugated with 1,3-disubstituted pyrazole moiety were synthesized on reaction with semicarbazide, thiosemicarbazide, 3-amino-5-oxo-2-pyrazoline, cyanoacetohydrazide, 2-acetyl thiophene, p-chloroacetophenone, urea, thiourea and 1,3-dicarbonyl compounds, respectively, by using 1-(3-chlorophenyl)-3-(4-methoxyphenyl)-1H-pyrazole-4-carboxaldehyde (2) as starting material. The structures of all the newly synthesized products have been established on the basis of analytical and spectral data. The anti-inflammatory screening showed that most of the obtained compounds were found to have significant anti-inflammatory activities with prostaglandin inhibition at a dose level of 2.
2.Synthesis and antimicrobial evaluation of some new thiazole, thiazolidinone and thiazoline derivatives starting from 1-chloro-3,4-dihydronaphthalene-2-carboxaldehyde.
Bondock S1, Khalifa W, Fadda AA. Eur J Med Chem. 2007 Jul;42(7):948-54. Epub 2007 Jan 13.
The thiosemicarbazones (3 and 6) and N-arylidene cyanoacetohydrazide (12) were prepared and used as key intermediates for the synthesis of 4-thiazolidinones (4, 5, 7-9), thiazoles (10a,b and 11a-d) and thiazoline (13) derivatives. Treatment of 13 with a mixture of triethylorthoformate and acetic anhydride afforded thiazolo[5,4-d]pyrimidinone derivative (14). The newly synthesized compounds were characterized by IR, (1)H NMR and mass spectral studies. Representative compounds of the synthesized products were tested and evaluated as antimicrobial agents.
3.In vitro cytotoxcity and interaction of new steroidal oxadiazinanones with calf thymus DNA using molecular docking, gel electrophoresis and spectroscopic techniques.
Dar AM1, Ishrat U2, Yaseen Z3, Shamsuzzaman2, Gatoo MA4. J Photochem Photobiol B. 2015 Jul;148:340-50. doi: 10.1016/j.jphotobiol.2015.04.031. Epub 2015 May 14.
Herein we report synthesis of new steroidal oxadiazinanones from steroidal ketones. After characterization by spectral and analytical data, the interaction studies of compounds (4-6) with DNA were carried out by UV-vis, fluorescence spectroscopy and gel electrophoresis. The compounds bind to DNA preferentially through electrostatic and hydrophobic interactions with Kb; 1.8×10(4) M(-1), 2.2×10(4) M(-1) and 2.6×10(4) M(-1), respectively, indicating the higher binding affinity of compound 6 towards DNA. Gel electrophoresis showed the concentration dependent cleavage activity of compound 6 alone or in presence of Cu (II) causes the nicking of supercoiled pBR322 and it seems to follow the mechanistic pathway involving generation of hydroxyl radicals that are responsible for initiating DNA strand scission. Molecular simulations suggest that compounds binds through minor groove of DNA. MTT assay depicted promising anticancer activity of compound 5 and 6 particularly against HL-60 and MCF-7.
4.Synthesis and anti-tumor evaluation of novel hydrazide and hydrazide-hydrazone derivatives.
Wardakhan WW1, El-Sayed NN, Mohareb RM. Acta Pharm. 2013 Mar;63(1):45-57. doi: 10.2478/acph-2013-0004.
The reaction of cyclopentanone with cyanoacetylhydrazine gave 2-cyano-2-cyclopentylideneacetohydrazide (1). Treatment of compound 1 with elemental sulphur in the presence of triethylamine afforded 2-amino-5,6-dihydro- -4H-cyclopenta[b]thiophene-3-carbohydrazide (2), which in-turn formed the corresponding intermediate diazonium salt. The latter was coupled with either ethyl cyanoacetate or ethyl acetoacetate to form 2-cyano-2-(3-(hydrazinecarbonyl)- 5,6-dihydro-4H-cyclopenta[b]thiophen-2-yl)hydrazono) acetate (3) and ethyl 2-(2-(3-(hydrazinecarbonyl)-5,6-dihydro- 4H-cyclopenta[b]thiophen-2-yl)hydrazono)-3-oxobutanoate (4), respectively. On the other hand, the reaction of compound 1 with either benzaldehyde or acetophenone afforded N'-benzylidene-2-cyano-2-cyclopentylideneacetohydrazide (7) and 2-cyano-2-(2-cyclopentylidene)phenylacetohydrazide (10), respectively. Moreover, compound 1 was used to synthesize 2-cyano-2-cyclopentylidene- N'-(arylthiazol-2(3H)-ylidene)acetohydrazides (6a,b), 2-(2-benzylidenecyclopentylidene)-2-cyanoacetohydrazide (8), 2-amino-N'-benzylidene-5,6-dihydro-4H- -cyclopenta[b]thiophene-3-carbohydrazide (9), 2-cyano- -2-(2-(2-phenylhydrazono)cyclopentylidene)acetohydrazide (11), N'-(1-chloropropan-2-ylidene)-2-cyano-2-cyclopentylideneacetohydrazide (12), and 2-cyclopentylidene-3- -(3,5-disubstituted-1H-pyrazol-1-yl)-3-oxopropanenitriles (13a,b) through its reaction with the respective reagents.
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CAS 140-87-4 Cyanoacetohydrazide

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