Abstract
4-Amino-3-methyl-1-phenyl- 1H -thieno[2,3- c ]pyrazole-5-carboxamide has been synthesized by an innovative method. The aminoamide derivative was gently refluxed with chloroacetyl chloride under neat conditions followed by neutralization with sodium carbonate solution to afford the chloromethyl pyrimidinone compound. The chloromethyl pyrimidinone derivative was converted to the thiol derivative by the reaction with thiourea in ethanol. The thiol compound was alkylated with α-halocompounds such as ethyl chloroacetate, chloroacetone, phenacyl bromide and 2-chloro-4,6-dimethylnicotinonitrile to afford the corresponding S-alkylated compounds. The chemical structures of the newly synthesized compounds were elucidated on the basis of elemental and spectral analyses containing FT-IR, 1 H-NMR, and mass spectroscopy.
Highlights
Thieno[3,4-c]pyrazoles are a class of biologically active compounds, currently employed in the field of medicinal chemistry owing to their remarkable anti-inflammatory,7,8 analgesic and antithrombotic activities, for the treatment of cardiovascular or cerebrovascular diseases, and hyperglycemia
Thieno[3,2-c]pyrazoles are used in the treatment of hypertension and glaucoma
IR spectrum of compound [5] revealed appearance of absorption band at 3400, 3305, 3190 cm-1 due to two NH2 group. 1H NMR spectrum showed two singlet signals at δ 2.60, 6.90 and 7.00 ppm characteristic for CH3 and NH2 groups respectively. 13C NMR spectrum displayed signals at 15.2 and 169.80 ppm attributed to CH3 and CONH2 groups respectively
Summary
Many of pyrazoles and related compounds are known to possess biological activity. Thieno[3,4-c]pyrazoles are a class of biologically active compounds, currently employed in the field of medicinal chemistry owing to their remarkable anti-inflammatory, analgesic and antithrombotic activities, for the treatment of cardiovascular or cerebrovascular diseases, and hyperglycemia. Thieno[3,2-c]pyrazoles are used in the treatment of hypertension and glaucoma. Thieno[2,3c]pyrazoles on the other hand, represent a class of heterocyclic compounds which have antifungal, antibacterial and anti-inflammatory activities.. Many of pyrazoles and related compounds are known to possess biological activity.. Thieno[3,4-c]pyrazoles are a class of biologically active compounds, currently employed in the field of medicinal chemistry owing to their remarkable anti-inflammatory, analgesic and antithrombotic activities, for the treatment of cardiovascular or cerebrovascular diseases, and hyperglycemia.. Thieno[3,2-c]pyrazoles are used in the treatment of hypertension and glaucoma.. Thieno[2,3c]pyrazoles on the other hand, represent a class of heterocyclic compounds which have antifungal, antibacterial and anti-inflammatory activities.. IR spectrum of compound [5] revealed appearance of absorption band at 3400, 3305, 3190 cm-1 due to two NH2 group. 1H NMR spectrum showed two singlet signals at δ 2.60, 6.90 and 7.00 ppm characteristic for CH3 and NH2 groups respectively. 13C NMR spectrum displayed signals at 15.2 and 169.80 ppm attributed to CH3 and CONH2 groups respectively IR spectrum of compound [5] revealed appearance of absorption band at 3400, 3305, 3190 cm-1 due to two NH2 group. 1H NMR spectrum showed two singlet signals at δ 2.60, 6.90 and 7.00 ppm characteristic for CH3 and NH2 groups respectively. 13C NMR spectrum displayed signals at 15.2 and 169.80 ppm attributed to CH3 and CONH2 groups respectively
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