86799-26-0

Basic information

• Product Name: 2,4(1H,3H)-Pyrimidinedione, 6-phenyl-, 2-hydrazone
• CAS NO: 86799-26-0
• Molecular Formula: C10H10N4O
• Molecular Weight: 202.216
• Mol File: 86799-26-0.mol

Chemical Properties

• CAS DataBase Reference: 2,4(1H,3H)-Pyrimidinedione, 6-phenyl-, 2-hydrazone(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4(1H,3H)-Pyrimidinedione, 6-phenyl-, 2-hydrazone(86799-26-0)
• EPA Substance Registry System: 2,4(1H,3H)-Pyrimidinedione, 6-phenyl-, 2-hydrazone(86799-26-0)

Safety Data

• Hazardous Substances Data: 86799-26-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research and Drug Development:
2,4(1H,3H)-Pyrimidinedione, 6-phenyl-, 2-hydrazone serves as a key intermediate in the synthesis of various pharmaceutical compounds and biologically active molecules. Its unique structure and functional groups enable the creation of diverse drug candidates with potential therapeutic applications.
Used in Organic Synthesis:
In the field of organic synthesis, 2,4(1H,3H)-Pyrimidinedione, 6-phenyl-, 2-hydrazone is utilized as a valuable building block for the preparation of complex organic molecules. Its reactivity and structural features facilitate the formation of a wide range of chemical products, contributing to the advancement of organic chemistry.
Used in Medicinal Chemistry:
2,4(1H,3H)-Pyrimidinedione, 6-phenyl-, 2-hydrazone plays a significant role in medicinal chemistry, where it is employed as a starting material for the design and synthesis of novel drug candidates. Its diverse pharmacological activities and potential for further functionalization make it an attractive scaffold for the development of new therapeutic agents.

Upstream product

• 36822-11-4 6-phenyl-2-thiouracil 
• 56035-29-1 2-methylthio-6-phenyl-3,4-dihydropyrimidin-4-one 
• 56741-96-9 3,4-Dihydro-2-(nitroamino)-6-phenylpyrimidin-4-one 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 36822-11-4 2-mercapto-6-phenylpyrimidin-4(3H)-one 
• 56035-29-1 6-Phenyl-2-S-methylpyrimidine-4-one 

Downstream Products

• 107151-82-6 benzaldehyd-(6-oxo-4-phenyl-1,6-dihydro-pyrimidin-2-ylhydrazone) 
• 1612261-37-6 6-phenyl-2-(2-(propan-2-ylidene)hydrazinyl)pyrimidin-4(3H)-one 
• 1612261-41-2 2-(2-cyclopentylidenehydrazinyl)-6-phenylpyrimidin-4(3H)-one 
• 1612261-45-6 2-(2-(3-methylcyclopentylidene)hydrazinyl)-6-phenylpyrimidin-4(3H)-one 

Relevant articles and documents

Antitubercular 2-Pyrazolylpyrimidinones: Structure-Activity Relationship and Mode-of-Action Studies

Phenotypic screening of a Medicines for Malaria Venture compound library against Mycobacterium tuberculosis (Mtb) identified a cluster of pan-active 2-pyrazolylpyrimidinones. The biology triage of these actives using various tool strains of Mtb suggested a novel mechanism of action. The compounds were bactericidal against replicating Mtb and retained potency against clinical isolates of Mtb. Although selected MmpL3 mutant strains of Mtb showed resistance to these compounds, there was no shift in the minimum inhibitory concentration (MIC) against a mmpL3 hypomorph, suggesting mutations in MmpL3 as a possible resistance mechanism for the compounds but not necessarily as the target. RNA transcriptional profiling and the checkerboard board 2D-MIC assay in the presence of varying concentrations of ferrous salt indicated perturbation of the Fe-homeostasis by the compounds. Structure-activity relationship studies identified potent compounds with good physicochemical properties and in vitro microsomal metabolic stability with moderate selectivity over cytotoxicity against mammalian cell lines.

Evaluation of a large library of (thiazol-2-yl)hydrazones and analogues as histone acetyltransferase inhibitors: Enzyme and cellular studies

Recently we described some (thiazol-2-yl)hydrazones as antiprotozoal, antifungal and anti-MAO agents as well as Gcn5 HAT inhibitors. Among these last compounds, CPTH2 and CPTH6 showed HAT inhibition in cells and broad anticancer properties. With the aim to identify HAT inhibitors more potent than the two prototypes, we synthesized several new (thiazol-2-yl)hydrazones including some related thiazolidines and pyrimidin-4(3H)-ones, and we tested the whole library existing in our lab against human p300 and PCAF HAT enzymes. Some compounds (1x, 1c', 1d', 1i' and 2m) were more efficient than CPTH2 and CPTH6 in inhibiting the p300 HAT enzyme. When tested in human leukemia U937 and colon carcinoma HCT116 cells (100 μM, 30 h), 1x, 1i' and 2m gave higher (U937 cells) or similar (HCT116 cells) apoptosis than CPTH6, and were more potent than CPTH6 in inducing cytodifferentiation (U937 cells).

Synthesis of pyrimidine, thiazolopyrimidine, pyrimidotriazine and triazolopyrimidine derivatives and their biological evaluation

Pyrimidin-4-one-2-thione (3) was synthesized via the reaction of thiourea (1) with ethyl henzoylacetate (2) and was taken as a starting material for the present study via its reactions with the halogen-containing reagents 6a-d and 10a-c to give the corresponding thiazolopyrimidines 8, 9 and 12a-c. The 2-hydrazino derivatives 5 were synthesized either via the reaction of 3 or 4 with hydrazine hydrate. Compound 5 reacted with 6a-c and 10a-c to give the corresponding pyrimidotriazines 17a-c and 19 respectively. Also, compound 5 reacted with the active methylene-containing reagents 13 and 2a,b to give the corresponding 2-pyrazolopyrimidines 15 and 22a,b respectively. On the other hand, the triazolopyrimidines 21a,b and 30a,b were also obtained via the reaction of 5 with each of formic acid, acetic anhydride, ethyl chloroformate and carbon disulfide respectively. Some of the newly synthesized heterocyclic derivatives were tested for their biological activity.