Furo&Thieno[n,m-a]Pyridine&Pyrimidine

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Introduction

Thienopyrimidine is a bi-heterocyclic compound composed of a five-membered thiophene nucleus and a six-membered pyrimidine nucleus, which is an analogue of purine and an antagonist of human nucleic acid metabolism. Compounds with thienopyrimidine ring structure have extensive and significant biological and pharmacological activities, and have attracted people's attention as early as the 1970s. Generally, thienopyrimidine (C6H4N2S) has three structures, namely thieno[2,3-d]pyrimidine, thieno[3,2-d]pyrimidine, and thieno[3,4-c]pyrimidine. As organic chemicals, the applications of thienopyrimidine and its derivatives are as follows:

Synthesis of Antitumor DrugsSynthesis of Bacteriostatic CompoundsSynthesis of Pesticides
Wang et al. synthesized new fused thieno[2,3-d] pyrimidine-4(3H)-one derivatives with different substitutions by Wittig reaction, and the in vitro activity test showed that these compounds have good anti-tumor activity [1].Zhou et al. synthesized fluorine-containing thienopyrimidinone derivatives by Gewald reaction and Wittig reaction. The antibacterial activity test results show that the products have good inhibitory effects on cotton fusarium wilt, rice sheath blight, and cotton anthracnose [2].Most thienopyrimidine compounds have low toxicity to mammals, fish and birds, and high selectivity to pests and pathogens, which opens up a broad development space for the research and development of new pesticides.

Furopyrimidines are a class of organic compounds with furan and pyrimidine rings. Generally, furanopyrimidines have three structures, namely furo[2,3-d] pyrimidines, furo[3,2-d] pyrimidines and furo[3,4-b] pyrimidines.

Furopyrimidine derivatives. Figure 1. Furopyrimidine derivatives.

Fused pyrimidinone derivatives have abundant and diverse chemical properties, and more importantly, have good biological activities. For example, benzofuran pyrimidine derivatives (compound 1) exhibit broad-spectrum biological activities such as bactericidal, antiviral, anti-inflammatory, antitumor, and analgesic and hypoglycemic effects [3]. Benzofuran isoquinoline (compound 2) has potential analgesic effect [4]. Bicyclic nucleoside analogs (compound 3) interacting with nucleic acid carriers are applied to automatic fluorescent nucleoside probes. Compound 3 [5] as well as potential and highly selective Varicella-Zoster Virus inhibitors for positron propagation tomography and thymidine kinase gene expression imaging. Compound 4 [6] has broad antiviral activity as a folate antagonist.

If you are interested in our furo&thieno[n,m-a]pyridine&pyrimidine products, please contact us immediately!

References

  1. Wang, H.M. et al. Synthesis and antitumor activity of some novel 5, 6, 7, 8-tetra-hydro-benzo-thieno[2, 3-d]pyrimidin-4(3H)-one derivatives. Chin. J. Org. Chem. 2015, 35: 1075.
  2. Zhou, X. et al. Synthesis and antibacterial activities of novel thieno pyrimidine ketone derivatives. Chin. J. Syn. Chem. 2015, 23: 411.
  3. Bereznak, J. et al. Fungiciadl pyrimidinones.US006066638A.
  4. Weller, D. et al. Synthesis of 3-methyl-5,6-dihydro-3H-benzofuro [3,2-e] isoquinolin-7(7H)-ones. J. Org. Chem. 1983, 24: 4597-4605.
  5. McGuigan, C. et al. Highly potent and selective inhibition of varicella-zoster virus by bicyclic furopyrimidine nucleosides bearing an aryl side chain. J. Med. Chem. 2000, 43: 4993-4997.
  6. Gangjee, A. et al. CoMFA and CoMSIA analyses of pneumocystis carinii dihydrofolate reductase,toxoplasma gondii dihydrofolate reductase, and rat liver dihydrofolate reductase. J. Med. Chem. 2005, 48: 1448-1469.

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