☆ 4.2 Article

Synthesis of Two New Heterocyclic Systems: Furo[3′,2′:5,6]pyrimido[2,1-c][1,2,4]triazines and Furo[3,2-e][1,2,3,4]tetrazolo[1,5-a]pyrimidine

JOURNAL OF THE IRANIAN CHEMICAL SOCIETY (2011)

Journal

JOURNAL OF THE IRANIAN CHEMICAL SOCIETY

Volume 8, Issue 4, Pages 1135-1138

Publisher

IRANIAN CHEMICAL SOC

DOI: 10.1007/BF03246571

Keywords

Furo[2,3-d]pyrimidine; alpha-Haloketones; Triazines; Tetrazole

Categories

Chemistry, Multidisciplinary

Funding

Ferdowsi University of Mashhad Research Council

Ask authors/readers for more resources

Protocol

Community support

Reagent

Community support

Abstract

Two novel heterocyclic triazines and tetrazole systems were synthesized through cyclization of 2-hydrazino-furo[2,3-d]pyrimidine with alpha-haloketones and nitrous acid respectively in high yields. The starting 2-hydrazino-pyrimidine was synthesized from 4-imino-3,6-diphenyl-furo[2,3-d]pyrimidine-2(1H)-thione by methylation and subsequent nucleophilic displacement of methylthio group with hydrazine hydrate.

Authors

I am an author on this paper

Click your name to claim this paper and add it to your profile.

Reviews

Primary Rating

4.2

Not enough ratings

Secondary Ratings

Novelty

-

Significance

-

Scientific rigor

-

Rate this paper

Recommended

Article Chemistry, Organic

Tandem ring-opening and formal [3+2] cycloaddition of furo[2,3-d]pyrimidine-2,4-diones

Li Huang, Ying Han, Jing Sun, Qiu Sun, Chao-Guo Yan

Summary: The base promoted tandem annulation reaction of activated cyclic 1,3-dipolarophiles with functionalized furo[2,3-d]pyrimidine-2,4-diones provided efficient synthetic protocols for complex dispiro/dispiro fused tricyclic compounds. This reaction proceeded via sequential ring-opening, formal [3 + 2] cycloaddition, and annulation processes.

ORGANIC & BIOMOLECULAR CHEMISTRY (2023)

Add to Collection

Article Biochemistry & Molecular Biology

Design and synthesis of novel furan, furo[2,3-d]pyrimidine and furo[3,2-e] [1,2,4]triazolo[1,5-c]pyrimidine derivatives as potential VEGFR-2 inhibitors

Menna M. A. Abd El-Mageed, Amal A. M. Eissa, Awatef El-Said Farag, Essam Eldin A. Osman

Summary: A series of novel furan and furo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidine derivatives were designed and synthesized, exhibiting good to moderate VEGFR-2 inhibitory activity. Some compounds showed higher antiproliferative effects on HUVECs compared to sorafenib, with the ability to disrupt cell cycle progression and inhibit cell invasion and migration.

BIOORGANIC CHEMISTRY (2021)

Add to Collection

Article Chemistry, Organic

Synthesis and anticancer activities of diverse furo[2,3-d]pyrimidine and benzofuro[3,2-d]pyrimidine derivatives

Xiaoyu Tang, Aihua Zheng, Fengxu Wu, Chujie Liao, Yanggen Hu, Chao Luo

Summary: A series of diverse furo[2,3-d]pyrimidines and benzofuro[3,2-d]pyrimidines were synthesized and screened for their antitumor effects. Compound 4a showed the best activity against HepG2 cell lines and was found to have possible binding modes with receptor tyrosine kinase.

SYNTHETIC COMMUNICATIONS (2022)

Add to Collection

Article Biochemistry & Molecular Biology

Design, synthesis, and biological evaluation of pyrido[2,3-d]pyrimidine and thieno[2,3-d]pyrimidine derivatives as novel EGFRL858R/T790M inhibitors

Jianfang Fu, Jie Yu, Xiang Zhang, Yaoyao Chang, Hongze Fan, Mengzhen Dong, Mengjia Li, Yue Liu, Jinxing Hu

Summary: In this study, two series of EGFR kinase inhibitors were designed and synthesised. Compound B1 showed selective inhibition against EGFR (L858R/T790M) with an IC50 value of 13 nM and a 76-fold selectivity for EGFR (WT). In vitro experiments demonstrated that compound B1 effectively inhibited proliferation of H1975 cells with an IC50 value of 0.087 μM. Mechanistic studies confirmed the selective inhibition of EGFR (L858R/T790M) by compound B1 through cell migration and apoptosis assays.

JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY (2023)

Add to Collection

Article Chemistry, Multidisciplinary

Identification of novel furo[2,3-d]pyrimidine based chalcones as potent anti-breast cancer agents: synthesis, in vitro and in vivo biological evaluation

Mai A. Mansour, Mamdouh A. Oraby, Zeinab A. Muhammad, Deena S. Lasheen, Hatem M. Gaber, Khaled A. M. Abouzid

Summary: Synthetic furo[2,3-d]pyrimidine-based chalcones exhibited potent anti-proliferative and cytotoxic activities against cancer cells. Among the halogen-bearing derivatives, compounds 5d and 5e showed significant anti-proliferative activity against a resistant cell line and comparable efficacy to doxorubicin in in vivo anticancer assessment.

RSC ADVANCES (2022)

Add to Collection

Article Chemistry, Multidisciplinary

Microwave Assisted Synthesis of 2,3-Dihydro-4H- furo[2,3-d]pyrido[1,2-a]pyrimidin-4-ones and furo[2,3-d]pyrido[1,2-a]pyrimidin-4-one

Sumeyye Yalduz, Mehmet Yilmaz

Summary: In this study, furo[2,3-d]pyrido[1,2-a]pyrimidin-4-ones were synthesized by microwave-assisted radical cyclizations. The reaction was performed between 2-hydroxy-4H-pirido[1,2-a]pirimidin-4-ones and conjugated alkenes and phenylacetylene using Mn(OAc)(3) as a catalyst. Different reaction conditions were compared to optimize the reaction. The obtained compounds were characterized using spectroscopic techniques and XRD analysis.

CHEMISTRYSELECT (2023)

Add to Collection

Article Biochemistry & Molecular Biology

Discovery of new thieno[2,3-d]pyrimidine and thiazolo[5,4-d]pyrimidine derivatives as orally active phosphoinositide 3-kinase inhibitors

Yan Sun, Rong Fu, Songwen Lin, Jingbo Zhang, Ming Ji, Yan Zhang, Deyu Wu, Kehui Zhang, Hua Tian, Mingyi Zhang, Li Sheng, Yan Li, Jing Jin, Xiaoguang Chen, Heng Xu

Summary: A new series of PI3K inhibitors were designed and synthesized, showing promising anti-cancer activity and in vivo efficacy. Among them, thiazolo [5,4-d]pyrimidine 7a demonstrated superior anti-cancer activity compared to other compounds, warranting further pre-clinical evaluation.

BIOORGANIC & MEDICINAL CHEMISTRY (2021)

Add to Collection

Article Biochemistry & Molecular Biology

SnAr Reactions of 2,4-Diazidopyrido[3,2-d]pyrimidine and Azide-Tetrazole Equilibrium Studies of the Obtained 5-Substituted Tetrazolo[1,5-a]pyrido[2,3-e]pyrimidines

Kristaps Leskovskis, Anatoly Mishnev, Irina Novosjolova, Maris Turks

Summary: We have developed a straightforward method for the synthesis of 5-substituted tetrazolo[1,5-a]pyrido[2,3-e]pyrimidines from 2,4-diazidopyrido[3,2-d]pyrimidine through SnAr reactions with N-, O-, and S- nucleophiles. The N- and S-substituted products were obtained in good yields (47% to 98%), while the substitution with O-nucleophiles gave lower yields (20-32%). The fused tetrazolo[1,5-a]pyrimidine derivatives can be functionalized through copper(I)-catalyzed azide-alkyne dipolar cycloaddition (CuAAC) and Staudinger reactions due to the presence of a sufficient concentration of the reactive azide tautomer.

MOLECULES (2022)

Add to Collection

Article Biochemistry & Molecular Biology

Design, combinatorial synthesis and cytotoxic activity of 2-substituted furo[2,3-d]pyrimidinone and pyrrolo[2,3-d]pyrimidinone library

Buer Song, Lifei Nie, Khurshed Bozorov, Rustamkhon Kuryazov, Jiangyu Zhao, Haji Akber Aisa

Summary: A facile one-pot condensation protocol was developed for the combinatorial synthesis of furo[2,3-d]pyrimidinone and pyrrolo[2,3-d]pyrimidinone library from 2-amino furans/pyrroles. Both furo[2,3-d]pyrimidinones and pyrrolo[2,3-d]pyrimidinones exhibited anticancer activity against human cancer cell lines, with derivative 12n showing high activity against HeLa cell line.

MOLECULAR DIVERSITY (2023)

Add to Collection

Article Biochemistry & Molecular Biology

Exploration of 4-aminopyrrolo[2,3-d]pyrimidine as antitubercular agents

Omobolanle Janet Jesumoroti, Richard M. Beteck, Audrey Jordaan, Digby F. Warner, Lesetja J. Legoabe

Summary: Tuberculosis (TB) is a major cause of death worldwide. In this study, a library of 7H-Pyrrolo[2,3-d]pyrimidine derivatives was synthesized to develop new anti-TB compounds. Sixteen compounds showed activity against Mycobacterium tuberculosis, with the most potent derivative having a MIC90 value of 0.488 μM and no cytotoxicity. These findings suggest that these compounds have potential for further drug development and optimization.

MOLECULAR DIVERSITY (2023)

Add to Collection

Article Biochemistry & Molecular Biology

Versatile anti-infective properties of pyrido- and dihydropyrido[2,3-d] pyrimidine-based compounds

Ibrahim S. Al Nasr, Angela Corona, Waleed S. Koko, Tariq A. Khan, Ridha Ben Said, Ismail Daoud, Seyfeddine Rahali, Enzo Tramontano, Rainer Schobert, Noureddine Amdouni, Bernhard Biersack

Summary: A series of 1H-indeno[2',1'-5,6]dihydropyrido[2,3-d]pyrimidine and 1H-indeno[2',1'-5,6]pyrido[2,3-d]pyrimidine derivatives were synthesized and screened for their activity against parasites and viral RNase H. Some compounds exhibited significant activity against Toxoplasma gondii parasites and Leishmania major amastigotes, suggesting further investigation is warranted. A HIV-1 RNase H assay was used to study the RNase H inhibition of selected compounds, and docking simulations were performed to investigate their binding to the active site of the HIV-1 RNase H enzyme. Compound 2a, which was inactive against parasites, showed distinct HIV-1 RNase H inhibitory activity, suggesting that ring substitution determines the antiparasitic or HIV-1 RNase H inhibitory activity of this compound class.

BIOORGANIC & MEDICINAL CHEMISTRY (2023)

Add to Collection

Article Chemistry, Medicinal

Identification of novel Pyrrolo[2,3-d]Pyrimidine-based KRAS G12C inhibitors with anticancer effects

Zhendong Song, Linlin Lou, Guangjin Fan, Lu Liu, Yang Ge, He Liu, Albert S. C. Chan, Xiaolei Zhang, Xiao-Feng Xiong

Summary: Oncogene KRAS plays important roles in human cancers by regulating cell proliferation, differentiation, and migration. Recent advancements have shown that targeting KRAS G12C directly with allosteric inhibitors that bind to the switch II pocket is feasible. In this study, a series of pyrrolo[2,3-d]pyrimidine derivatives were designed and synthesized, leading to the discovery of compound 50 with high KRAS/SOS1 inhibitory potency and strong anti-proliferation activities on cancer cells harboring KRAS p.G12C. Compound 50 also exhibited satisfactory selectivity, moderate pharmacokinetic characteristics, and good anticancer effects in vivo.

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY (2023)

Add to Collection

Article Chemistry, Physical

Structural study of azide-tetrazole equilibrium in pyrido[2,3-d]pyrimidines

Kristaps Leskovskis, Anatoly Mishnev, Irina Novosjolovaa, Maris Turks

Summary: C-5 substituted pyrido[3,2-e]tetrazolo[1,5-a]pyrimidines were synthesized by azidation and subsequent SNAr reactions. Their physical properties were characterized by NMR, IR, and X-ray analysis, revealing different forms and tautomers. The amino derivatives mainly exist in the tetrazole form and can undergo further reactions.

JOURNAL OF MOLECULAR STRUCTURE (2022)

Add to Collection

Article Chemistry, Physical

Efficient synthesis and cytotoxic activity of polysubstituted thieno[2,3-d]pyrimidine derivatives

Tianshuai Wang, Fengxu Wu, Lun Luo, Yan Zhang, Junkai Ma, Yanggen Hu

Summary: The fused heterocyclic ring system of thienopyrimidine scaffold has been widely used in pharmaceuticals to enhance pharmacological and biological activities. In this study, polysubstituted thieno[2,3-d]pyrimidine derivatives were synthesized and tested for their cytotoxic activity against Hela and A549 cancer cell lines. Compound 8c showed promising activity similar to the lead drug Olmutinib, and its binding to EGFR kinase differed from Olmutinib. The preliminary structure-activity relationship suggested that introducing oxygen substituents favored antitumor activity.

JOURNAL OF MOLECULAR STRUCTURE (2022)

Add to Collection

Article Chemistry, Organic

Palladium-Catalyzed Highly Regioselective C6 Arylation of Pyrrolo[2,3-d]pyrimidine Derivatives with Arylboronic Acids

Min Liu, Chunwei Shen, Ting Tang, Chenhong Pan, Mingrui Liu, Xingxian Zhang

Summary: This article describes a mild and selective C6 arylation strategy for pyrrolo[2,3-d]pyrimidine derivatives using arylboronic acids at room temperature. The unified protocol combines Pd(II)/TEMPO catalysis and CF3CO2H promotion under silver-, base-, and additive-free conditions. The broad substrate scope, good functional group tolerance, excellent regioselectivity, and air and moisture tolerant conditions make this process attractive for the effective synthesis and modification of targeted small molecule drugs.

ORGANIC LETTERS (2023)

Add to Collection

Article Chemistry, Organic

Synthesis of new derivatives of 10H-benzo[b]pyridazino[3,4-e][1,4]thiazines

Zahra Arghiani, Seyed Mohammad Seyedi, Mehdi Bakavoli, Mohsen Nikpour

HETEROCYCLIC COMMUNICATIONS (2015)

Add to Collection

Article Chemistry, Organic

Synthesis, Characterization, and Docking Evaluations of New Derivatives of Pyrimido[4,5-c]pyridazine as Potential Human AKT1 Inhibitors

Ayla Hazrathoseyni, Seyed Mohammad Seyedi, Hossein Eshghi, Ali Shiri, Mohammad Saadatmandzadeh, Ali Reza Berenji

JOURNAL OF HETEROCYCLIC CHEMISTRY (2016)

Add to Collection

Article Chemistry, Multidisciplinary

Synthesis of [1,2,4]triazolo[4,3:1′,6′]pyrimido[4′,5′:3,4]pyridazino[1,6-d] [1,2,4]triazine; a novel tetracyclic system

Ayla Hazrathoseyni, Seyed Mohammad Seyedi, Ali Shiri, Hossein Eshghi

JOURNAL OF CHEMICAL RESEARCH (2015)

Add to Collection

Article Chemistry, Applied

Magnetically recoverable lanthanum hydroxide as an efficient catalyst for Aerobic Oxidative Conversions of primary alcohols to the nitriles

Fariborz Ziaee, Mostafa Gholizadeh, Seyed Mohammad Seyedi

APPLIED ORGANOMETALLIC CHEMISTRY (2018)

Add to Collection

Article Biochemistry & Molecular Biology

A novel class of human 15-LOX-1 inhibitors based on 3-hydroxycoumarin

Seyed Jamal Alavi, Hamid Sadeghian, Seyed Mohammad Seyedi, Alireza Salimi, Hossein Eshghi

CHEMICAL BIOLOGY & DRUG DESIGN (2018)

Add to Collection

Article Chemistry, Multidisciplinary

Fe(HSO4)3•SiO2 as an efficient, heterogeneous and recyclable catalyst for the synthesis of bis-(β-enaminones) and bis-(β-enamino esters)

Hossein Eshghi, Elham Safaei, Seyed Mohamad Seyedi, Tahereh Eshghi

COMPTES RENDUS CHIMIE (2014)

Add to Collection

Article Chemistry, Organic

Facile Synthesis of New [1,2,4]Triazolo[4,3-b]pyridazine

Z. Arghiani, S. M. Seyedi, M. Bakavoli, H. Eshghi

JOURNAL OF HETEROCYCLIC CHEMISTRY (2015)

Add to Collection

Article Chemistry, Physical

Silica supported Fe(HSO4)3 as an efficient, heterogeneous and recyclable catalyst for synthesis of β-enaminones and β-enamino esters

Hossein Eshghi, Seyed Mohammad Seyedi, Elham Safaei, Mohammad Vakili, Abolghasem Farhadipour, Mohtaram Bayat-Mokhtari

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL (2012)

Add to Collection

Article Chemistry, Multidisciplinary

Nanomagnetically modified ferric hydrogen sulfate (NiFe2O4@SiO2-FHS): a reusable green catalyst for the synthesis of highly functionalized piperidine derivatives

Mohammad Rahimizadeh, Seyed Mohammad Seyedi, Mohsen Abbasi, Hossein Eshghi, Amir Khojastehnezhad, Farid Moeinpour, Mehdi Bakavoli

JOURNAL OF THE IRANIAN CHEMICAL SOCIETY (2015)

Add to Collection

Article Chemistry, Multidisciplinary

Ionic liquids bis(2-N-methylimidazoliumethyl)ether dichloroiodate/dibromochlorate as an efficient halogenating reagent for the synthesis of α-haloketones

Hossein Eshghi, Mehdi Bakavoli, Marjan Ghasemzadeh, Seyed Mohammad Seyedi

RESEARCH ON CHEMICAL INTERMEDIATES (2015)

Add to Collection

Article Chemistry, Multidisciplinary

Synthesis of new derivatives of pyrimido[5,4-e][1,2,4]triazolo[3,4-b][1,3,4]thiadiazine and their enzyme inhibitory activity assessment on soybean 15-lipoxygenase

Mehdi Bakavoli, Seyed Mohammad Seyedi, Ali Shiri, Sattar Saberi, Mahmoud Gholami, Hamid Sadeghian

JOURNAL OF CHEMICAL RESEARCH (2013)

Add to Collection

Article Chemistry, Multidisciplinary

Synthesis, characterization and first application of keggin-type heteropoly acids supported on silica coated NiFe2O4 as novel magnetically catalysts for the synthesis of tetrahydropyridines

Hossein Eshghi, Amir Khojastehnezhad, Farid Moeinpour, Mehdi Bakavoli, Seyed Mohammad Seyedi, Mohsen Abbasi

RSC ADVANCES (2014)

Add to Collection

Article Chemistry, Applied

Zirconium (IV) porphyrin graphene oxide: a new and efficient catalyst for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones

Zohreh Ghadamyari, Ali Shiri, Amir Khojastehnezhad, Seyed Mohammad Seyedi

APPLIED ORGANOMETALLIC CHEMISTRY (2019)

Add to Collection

Article Chemistry, Applied

Cu Nano particles immobilized on silk-fibroin as a green and biodegradable catalyst for copper catalyzed azide-terminal, internal alkynes cycloaddition

Hakimeh Mirzaei, Hossein Eshghi, Seyed Mohammad Seyedi

Summary: The copper immobilized on silk fibroin was successfully prepared and characterized using multiple techniques, showing good catalytic activity in the azide-alkyne cycloaddition reaction under mild conditions. The heterogeneous-supported Cu catalyst showed stable catalytic activity after being reused four times.

APPLIED ORGANOMETALLIC CHEMISTRY (2021)

Add to Collection

Article Chemistry, Applied

Magnetically recoverable AlFe/Te nanocomposite as a new catalyst for the facile esterification reaction under neat conditions

Seyed Jamal Alavi, Hamid Sadeghian, Seyed Mohammad Seyedi, Hossein Eshghi, Alireza Salimi

APPLIED ORGANOMETALLIC CHEMISTRY (2018)

Add to Collection

No Data Available

© Peeref 2019-2024. All rights reserved.