109552-71-8

Upstream product

• 70638-56-1 5-cyano-6-(4-chlorophenyl)-2-thiouracil 
• 74-88-4 methyl iodide 
• 128061-80-3 4-(4-chlorophenyl)-2-(methylsulfanyl)-6-oxo-1,6-dihydropyrimidine-5-carbonitrile 

Downstream Products

• 389614-64-6 2-hydrazino-1-methyl-6-oxo-4-(4-chlorophenyl)-1,6-dihydropyrimidine-5-carbonitrile 

Relevant academic research and scientific papers

Synthesis of some dihydropyrimidine-based compounds bearing pyrazoline moiety and evaluation of their antiproliferative activity

Two series of 2-(3,5-diaryl-4,5-dihydropyrazol-1-yl)-1-methyl-6-oxo-4- phenyl-1,6-dihydropyrimidine-5-carbonitriles 5a-h and 4-(4-chlorophenyl)-2-(3,5- diaryl-4,5-dihydropyrazol-1-yl)-1-methyl-6-oxo-1,6-dihydropyrimidine-5- carbonitriles 6a-h were synthesized via a cyclocondensation reaction of the corresponding 2-hydrazinopyrimidines 3a,b with the appropriate 2-propen-1-ones 4a-h. The target compounds were screened for their antiproliferative activity against A 549 (lung), HT 29 (colon), MCF 7 and MDA-MB 231 (breast) cell lines. The two most susceptible cell lines were the colon (HT 29) and breast (MDA-MB 231). Generally, the 4-unsubstitutedphenylpyrimidine derivatives 5a-h were more active than their 4-chlorophenylpyrimidine analogs 6a-h. Compounds 5e and 5g, showed high activity against three of the cell lines. The most active compound 5c possessed IC50 = 1.76 μM against A 549 cell line.

Novel dihydropyrimidines and its pyrazole derivatives: Synthesis and pharmacological screening

In the present study, we have synthesized novel dihydropyrimidines (1a-j), their dimethylated adducts (2a-j), and hydrazine derivatives (3a-j) of 2a-j and subsequently their pyrazole derivatives (4a-j). Elemental analysis, IR, 1H NMR and mass s

Synthesis and screening of substituted eugenol and paracetamol linked pyrimidines

Several 6-(substituted)-5-cyano-2-methylthio-3-N-methyl-3,4- dihydropyrimidin-4-ones 1a-e were treated with N-[4-(2-hydrazinyl-2-oxoethoxy) phenyl] acetamide and 2-[3-methoxy-4-(prop-2-en-1-yl) phenoxy] aceto hydrazide, to get 2a-e and 3a-e respectively. All the synthesized compounds were screened for their antimicrobial activity and were characterized by elemental analyses, IR, 1H NMR and mass spectral data.

Reaction of pyrimidinonethione derivatives: Synthesis of N-methyl-2-hydrizinopyrimidine-4-one, thiazolo[3,4-b] N-methylpyrimidinone; 2-(1-pyrazolonyl) N-methylpyrimidine-4-one and 2-hydrazino-N-methyl pyrimidine-4-one derivatives

6-Aryl-5-cyano-4-pyrimidinone-2-thion derivatives 1a-c reacted with methyl iodide (1:2) to give the corresponding 2-S,N-dimethyl pyrimidine-4-one derivatives 2a-c. Compounds 2a-c were in turn, reacted with hydrazine hydrate to give the sulfur free reaction products 3a-c. These reaction products were taken as the starting materials for the synthesis of several new heterocyclic derivatives. Reaction of 3a-c with acetic anhydride and formic acid gave pyrimido triazines 4a-c and 7a-c, respectively. Their reactions with active methylene containing reagents gave the corresponding 2-(1-pyrazonyl)-N-methyl pyrimidine derivatives 9a-c and 10a-c, respectively. Their reactions with aromatic aldehydes afforded the corresponding 2-hydrazono pyrimidine derivatives 11a-c. The structure of these reactions products were established based on both elemental analysis and spectral data studies.

Synthesis and biological evaluation of some new azetidinones and thiazolidinones

Reaction between 6-(4′-chlorophenyl)-5-cyano-2-mercapto-3,4-dihydropyrimidin-4-one1 and methyl iodide in presence of K2CO3 in DMF yields the 6-(4′-chlorophenyl)-5-cyano-3-N-methyl-2-methylthio-3,4- dihydropyrimidin-4-one 2, which on treatment with hydrazine hydrate affords the 6-(4′-chlorophenyl)-5-cyano-2-hydrazino-3-N-methyl-3,4- dihydropyrimidin-4-one 3. The 6-(4′-chlorophenyl)-5-cyano-3-N-methyl-2-substituted ben-zalhydrazino-3,4-dihydropyrimidin-4-ones 4 are synthesised by the condensation of 3 with different aryl aldehydes. Compound 4 on condensation with chloroacetyl chloride and thiolactic acid affords the corresponding 2-(4″-aryl-3″-chloro-2″-azetidinon-1′′-yl- amino)-6-(4′-chlorophenyl)-5-cyano-3-N-methyl-3, 4-dihydro-pyrimidin 4-ones 5a-1 and 2-(2″-aryl-5″-methyl-4″-thiazolidinon-3″-yl-amino)-6 -(4′-chlorophenyl)-5-cyano-3-N-methyl-3,4-dihydro-pyrimidin-4-ones 6a-1. All the products have been evaluated for their in vitro antimicrobial activity against several microbes and antitubercular activity against Mycobacterium tuberculosis H37 Rv.

Synthesis and biological evaluation of some new 3,4-dihydropyrimidin-4-ones

Condensation of 5-cyano-2-hydrazino-3-N-methyl-6-phenyl/p-chlorophenyl-3,4-dihydropyrimidin-4 -one (3a and 3b) with 2,4-bisalkyl/arylamino-6-chloro-s-triazine (4) gave the corresponding 2,4-bisalkyl/arylamino-6-[5′-cyano-3′-N-methyl]-6′-phenyl/p -chlorophenyl-3′,4′-dihydropyrimidin-4′-one-2′-yl-hyd razino-s-triazines (5a-n and 6a-n). The compounds 4 have been prepared by the condensation of cyanuric chloride and different alkyl/aryl amines. The reaction between 5-cyano-3-N-methyl-2-methylthio-6-phenyl/p-chlorophenyl-3,4-dihydropyrimidin- 4-one (2a and 2b) with hydrazine hydrate furnished 3a and 3b, respectively. The condensation of 6-phenyl/p-chlorophenyl/5-cyano-2-mercapto-3,4-dihydropyrimidin-4-one (1a and 1b) with methyl iodide yielded 2a and 2b, respectively. All the products have been evaluated in vitro for their antimicrobial activity against several microbes and antitubercular activity against Mycobacterium tuberculosis H37 Rv. Copyright

Chemotherapeutic Agents. XII - Synthesis of Pyrimidines and Fused Pyrimidines as Leishmanicides and Herbicides

Various bicyclic (2, 3) and tricyclic (4, 5) heterocycles were prepared by the reaction of 1a, c with dihaloalkanes and polynitrohalobenzene separately.Electrophilic substitution on 1a-c with different alkyl halides yielded mono and dialkyl pyrimidines (6-20).Nucleophilic substitution reactions on 18 and 21 with amine and hydrazine separately yielded 22-31, 21a, b and 41c.Reaction of 25a with ethyl ethoxymethylenecyanoacetate and chloroacetyl chloride separately provided bicyclic compounds 32 and 33.Condensation-cyclization of 25a with formic, acetic and nitrous acid separately yielded 34a, b and 35.Reaction of 26a with ethylthioglycolate and thiourea separately provided 36a and 39.The latter was alkylated with methyl iodide to 40.An attempt to cyclize 29a and 30a with thionyl chloride provided bicyclic compounds 37a, b and an uncyclic product 38.Some of the compounds were screened for leishmanicidal and herbicidal activities and a few of them exhibited significant activity.

Chemotherapeutical Agents, V. - Syntheses and Activities of Novel Pyrimidines Derived from 5-Cyano-6-aryl-2-thiouracil

The 5-cyano-6-aryl-2-thiouracils 1a-d were prepared for the syntheses of several other pyrimidine derivatives.In basic medium 1a reacted with picryl chloride yielding the unexpected benzothiazolo-pyrimidine 2.Heating a mixture of 1 and 1,2-dibromoethane i