3-Amino-8-hydroxy-4-imino-6-methyl-5-phenyl-4,5-dihydro-3H-chromeno [2,3-d ]pyrimidine: An Effecient Key Precursor for Novel Synthesis of Some Interesting Triazines and Triazepines as Potential Anti-Tumor Agents

doi:10.3390/molecules171011538

Paper

3-Amino-8-hydroxy-4-imino-6-methyl-5-phenyl-4,5-dihydro-3H-chromeno [2,3-d ]pyrimidine: An Effecient Key Precursor for Novel Synthesis of Some Interesting Triazines and Triazepines as Potential Anti-Tumor Agents

Published Sep 27, 2012 · M. Badrey, Sobhi M. Gomha

Molecules

Q1 SJR score

42

Citations

0

Influential Citations

Open Access PDF Full text Semantic Scholar

Abstract

A number of interesting heterocycles were prepared through interaction of the intermediate 3-amino-8-hydroxy-4-imino-6-methyl-5-phenyl-4,5-dihydro-3H-chromeno-[2,3-d]pyrimidine (1) and reagents such as hydrazonyl halides 2 to furnish triazine derivatives 4a–l. Reaction of 1 with phenacyl bromide afforded compound 5. Moreover, the title compound 1 was subjected to condensation with active methylene compounds (ethyl acetoacetate and ethyl benzoylacetate) to give triazipinones 8a,b. The condensation with aromatic aldehydes afforded either the triazole derivatives 10a–d or Schiff base 11. In addition, the behaviour of compound 1 towards activated unsaturated compounds namely dimethyl acetylene dicarboxylate and ethoxymethylenemalonitrile was studied and it was found to furnish the triazine 13 and triazepine derivative 15, respectively. Combination of title compound 1 with chlorinated active methylene compounds delivered the triazine derivatives 18a–c. Reaction of 1 with chloroacetonitrile furnished compound 20. The structures of the products were elucidated based on their microanalyses and spectroscopic data. Finally, the antitumor activity of the new compounds 4a and 8a against human breast cell MCF-7 line and liver carcinoma cell line HepG2 were recorded.

In Vitro Study

Study Snapshot

The key precursor 3-amino-8-hydroxy-4-imino-6-methyl-5-phenyl-4,5-dihydro-3H-chromeno-[2,3-d]pyrimidine efficiently synthesized various triazines and triazepines with potential anti-tumor activity against

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Sign up to use Study Snapshot

Consensus is limited without an account. Create an account or sign in to get more searches and use the Study Snapshot.

Create an account

Paper

3-Amino-8-hydroxy-4-imino-6-methyl-5-phenyl-4,5-dihydro-3H-chromeno [2,3-d ]pyrimidine: An Effecient Key Precursor for Novel Synthesis of Some Interesting Triazines and Triazepines as Potential Anti-Tumor Agents

Sign up to use Study Snapshot

References

Synthesis of New Heterocycles Derived from 3-(3-Methyl-1H-indol-2-yl)-3-oxopropanenitrile as Potent Antifungal Agents

New thiazoline and thiophene derivatives linked to indole moiety show potential as potent antifungal agents.

ENAMINONES AS BUILDING BLOCKS IN HETEROCYCLIC PREPARATIONS : SYNTHESIS OF NOVEL PYRAZOLES, PYRAZOLO〔3,4-d〕PYRIDAZINES, PYRAZOLO〔1,5-a〕PYRIMIDINES, PYRIDO〔2,3-d〕PYRIMIDINES LINKED TO IMIDAZO〔2,1-b〕THIAZOLE SYSTEM

Enaminones can be used as building blocks in organic synthesis and exhibit various biological activities, such as antitumor, antibacterial, and anticonvulsant properties.

A Convenient Ultrasound-Promoted Synthesis of Some New Thiazole Derivatives Bearing a Coumarin Nucleus and Their Cytotoxic Activity

Ultrasound irradiation effectively synthesizes novel thiazole derivatives with potent cytotoxic activity, including compound 5a, which shows promising potential for pharmaceutical applications.

Synthesis, Tautomeric Structure and Antimicrobial Activity of 3-Arylhydrazono-4-phenyl-[1,2,4]-triazepino[2,3-a]quinazoline-2,7(1H)-diones

3-Arylhydrazono-4-phenyl-[1,2,4]-triazepino[2,3-a]quinazoline-2,7(1H)-diones show moderate antimicrobial activity against bacteria, with predominantly hydrazone tautomeric form.

A Convenient Methods for Synthetic Isomeric Structures of Pyrimido-1,2,4-triazine Derivatives as Biocidal Agents.

Synthetic isomeric structures of pyrimido-1,2,4-triazine derivatives show potential as biocidal agents, with compound 7 showing highly biocidal effects compared to pipericillin and mycostatine.

Facile Synthesis of New Pyrazolopyrimidine Derivatives of Potential Biosignificant Interest

This study presents a facile route for the synthesis of new pyrazolopyrimidine derivatives with potential biosignificant interest, including antibacterial and antifungal activity.

Synthesis and evaluation of in vitro antitubercular activity and antimicrobial activity of some novel 4H-chromeno[2,3-d]pyrimidine via 2-amino-4-phenyl-4H-chromene-3-carbonitriles

Novel 4H-chromeno[2,3-d]pyrimidine derivatives show pronounced antitubercular and antimicrobial activities against Mycobacterium tuberculosis H37Rv and various bacteria and fungi.

Synthesis of Pyrimidines and Heteroannulated Pyrimidine Ring Systems

Pyrimidines can be synthesized and their heteroannulated ring systems can be formed through Dimroth-type rearrangement, yielding various isomers.

Synthesis of 4H-chromene, coumarin, 12H-chromeno[2,3-d]pyrimidine derivatives and some of their antimicrobial and cytotoxicity activities.

This study synthesized 4H-chromene, coumarin, and 12H-chromeno[2,3-d]pyrimidine derivatives and tested their antimicrobial and cytotoxicity activities.

Citations

Synthesis, Anti-Cancer Activity, Cell Cycle Arrest, Apoptosis Induction, and Docking Study of Fused Benzo[h]chromeno[2,3-d]pyrimidine on Human Breast Cancer Cell Line MCF-7

Fused chromenopyrimidines (3a and 4a) show potential anti-cancer activity by exhibiting cell cycle arrest and dual Bcl-2 and Mcl-1 inhibitory characteristics in human breast cancer cell line MCF-7.

Novel Bis-thiazoles with Pyridine and 1,4-Dihydropyridine Linkers as Potential Anti-Alzheimer Agents

Novel bis-hydrazonothiazoles with pyridine and 1,4-dihydropyridine linkers show potential as anti-Alzheimer agents, showing similar therapeutic potential to current drugs.

Design and synthesis of novel hybrids incorporating thiadiazole or thiazole-naphthalene: Anticancer assessment and molecular docking study

Novel 1,3,4-thiadiazole and 1,3-thiazole derivatives show promising anticancer activity and favorable oral bioavailability properties, making them promising candidates for further development as antitumor medicines.

Insights into Microwave Assisted Synthesis of Spiro-chromeno[2,3-d]pyrimidines Using PEG-OSO3H Catalyst: DFT study and their antiproliferative activity

Microwave-assisted synthesis of spirochromeno[2,3-d]pyrimidines using PEG-OSO3H catalyst is environmentally friendly and produces compounds with excellent antiproliferative activity against solid human tumor cell lines.

Syntheses and Molecular Docking Analysis of Some New Thiazole and Thiazine Derivatives as Three Armed Molecules with a Triazine Ring as a Core Component: A Search for anti-Obesity Agents

New thiazole and thiazine derivatives with a triazine moiety show potential as promising chemical scaffolds for developing future anti-obesity drug candidates.

Synthesis and Molecular Docking of Some Novel 3-Thiazolyl-Coumarins as Inhibitors of VEGFR-2 Kinase

Novel 3-thiazolyl-coumarins show potential as VEGFR-2 inhibitors, with compounds 6d and 6b showing greater anticancer activity than Sorafenib.

Synthesis, structure analysis, biological activity and molecular docking studies of some hydrazones derived from 4-aminobenzohydrazide

Compounds 1, 3, 5, and 6 show good antibacterial activity against bacteria, while compounds 2, 4, 7, and 8 show good antifungal activity against fungal strains.