Benzo[4’,5’]imidazo[2’,1’:6,1]pyrido[2,3-d]pyrimidines: Past and Present

AA Harutyunyan

doi:10.61927/igmin113

2 of 120

Lhamu Sherpa and Nandan Banerji

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The Antioxidant and Antidepressant Properties of Dietary Proteins Derived from Egg and Bean Extracts and Their Acute Toxicity: A Journey from Nutrition to Pharmacognosy

Amal El Hamsas El Youbi, Omaima Boudaia, Zineb Sekkout, Najat El Amrani and Driss Radallah

Science Group Research Article Article ID: igmin113

Benzo[4’,5’]imidazo[2’,1’:6,1]pyrido[2,3-d]pyrimidines: Past and Present

Organic Chemistry Computational Chemistry Biochemistry

AA Harutyunyan ^*

Affiliation

The Scientific Technological Centre of Organic and Pharmaceutical Chemistry of NAS RA 26, Azatutyan Ave., Yerevan, 0014, Armenia

DOI10.61927/igmin113 Fulltext HTML Fulltext PDF Cite this article

Abstract

Synthetic approaches to the construction of the heterocyclic benzo[4’,5’]imidazo[2’,1’:6,1]pyrido[2,3-d]pyrimidine system based on heterocyclizations of substituted benzimidazoles and a new alternative strategy based on 2,4,6-trisubstituted pyrimidinyl-5-propanoic acids are considered. The latter method has been shown to be a successful addition to previously described methods, since it allows one to bypass the significant limitations associated with the use of substituted benzimidazoles and allows the introduction of functional substituents at different positions of the heterocycle that are inaccessible by other methods. The available information on derivatives of this heterocyclic system and their biological properties is summarized.

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References

Jampilek J. Heterocycles in Medicinal Chemistry. Molecules. 2019 Oct 25;24(21):3839. doi: 10.3390/molecules24213839. PMID: 31731387; PMCID: PMC6864827.
Sharma PK, Amin A, Kumar M. A Review: Medicinally important nitrogen sulphur containing heterocycles. Open Med. Chem. J. 2020; 14:49-64.org/10.2174/1874104502014010049
Kabir E, Uzzaman M. A review on biological and medicinal impact of heterocyclic compounds. Results in Chemistry. 2022; 4:100606. doi.org/10.1016/j.rechem.2022.100606
Sharma V, Gupta M, Kumar P, Sharma A. A Comprehensive Review on Fused Heterocyclic as DNA Intercalators: Promising Anticancer Agents. Curr Pharm Des. 2021;27(1):15-42. doi: 10.2174/1381612826666201118113311. PMID: 33213325.
Jubete G, de la Bellacasa PR, Estrada-Tejedor R, Teixido J, Borrell JI. Pyrido[2,3-d]pyrimidin-7(8H)-ones: synthesis and biomedical applications. Molecules. 2019; 24:4161. doi.org/10.3390/molecules24224161
Tahlan S, Kumar S, Narasimhan B. Pharmacological significance of heterocyclic 1H-benzimidazole scaffolds: a review. BMC Chem. 2019 Aug 6;13(1):101. doi: 10.1186/s13065-019-0625-4. PMID: 31410412; PMCID: PMC6685272.
Xiong H, Yu Q, Ma H, Yu X, Ouyang Y, Zhang ZM, Zhou W, Zhang Z, Cai Q. Exploration of tricyclic heterocycles as core structures for RIOK2 inhibitors. RSC Med Chem. 2023 Jul 21;14(10):2007-2011. doi: 10.1039/d3md00209h. PMID: 37859717; PMCID: PMC10583808.
CA Chem. Substance Index. v.95, 6179CS. 1981.
Hunter AD. ACD/ChemSketch 1.0 (freeware); ACD/ChemSketch 2.0 and its tautomers,dictionary, and 3D plug-ins; ACD/HNMR 2.0; ACD/CNMR 2.0. Chem. Educ. Easton.1997;74(8):905-908.
Pyrimido[5’,4’:5,6]pyrido[1,2-a] Ger. Offen. Chem. Abstr. 1981; 95: P44732; 2.929. 414.
Electrophotographic recording material. Wiedemann W. (Hoechst A.-G.). Ger. Offen. DE3.502.689, 33 pp. Chem. Abstr. 1987; 106:41561j.
Electrophotographic recording material. Wiedemann W, Guenther D. (Hoechst A.-G.). Ger.Offen. Chem. Abstr. 1988; 108: DE 3.502.681;28:122003x.
Bogdanowicz-Szwed K, Czarny A. Synthesis of polyazaheterocycles by Michael addition of CH acids to a α,β-unsaturated nitriles. Synthesis of pyrido[1,2-a]benzimidazole and pyrimido[5′,4' : 5,6]pyrido[l,2-a]benzimidazole derivatives. J. prakt. Chem. 1993; 335:279. org/10.1002/prac.19933350311
Elwan NM. First synthesis of novel pentaheterocyclic ring system of 1,2,4-triazolo[2",3":6',1']pyrimido[4',5':2,3]pyrido[1,2-a] J. Heterocyclic Chem. 2004; 41:281. doi.org/10.1002/jhet.5570410222
El-Zohry MF, Mohamed TA, Hussein EM. Novel syntheses of some new 3,4- dihydrospiro{benzimidazo[1,2-a]pyridine-3,30-indolin}-20-one derivatives. Monatsh. Chem. 2009; 140:265. org/10.1007/s00706-008-0013-6
Harutyunyan AA. Synthesis of the derivatives of the new heterocyclic system 5,6-dihydrobenzo[4',5']imidazo[2',1':6,1]pyrido[2,3-d] Chem. J. Armenia. 2012; 65(2):257. https://arar.sci.am/publication/204311
Harutyunyan АA, Panosyan HA, Tamazyan RA, Ayvazyan AG. New derivatives of the benzo[4,5]imidazo[2',1':6,1]pyrido[2,3-d] Chem. J. Armenia. 2016; 69(3):266. https://arar.sci.am/publication/205621
Harutyunyan AA. Studies in the field of the pyrimidines and polycyclic azaheterocycles synthesis. The dissertation abstract of the doctor of chemical sciences. Armenia, Yerevan. 2017.
Harutyunyan AA. Syntheses and biological properties of benzo[4', 5']imidazo[2',1': 6,1]-pyrido[2,3-d]pyrimidines: mini-review. Chem. J. Armenia. 2018; 71(4):579. https://arar.sci.am/publication/206351
Harutyunyan AA, Gukasyan GT, Panosyan HA, Tamazyan RA, Ayvazyan AG, Grigoryan AG, Danagulyan GG. Synthesis of new derivatives of benzo[4',5']imidazo[2 ',1': 6,1]pyrido[2,3-d] Russ. J. Org. Chem. 2019; 55(11):1698. doi.org/10.1134/S1070428019110095
Harutyunyan AA, Israelyan SG, Safaryan MS, Hakobyan MR, Sumbatyan AS, Dilanyan SV. Synthesis and biological properties of derivatives of five- and six-membered azaheterocycles and their condensed systems. Brief review of research by the laboratory for the synthesis of anti-cancer compounds in 2019-2023. Some Successes Organic and Pharmaceutical Chemistry. Collection of works. Issue 4, p. 112-135 (in English). Armenia, Yerevan. 2023; ISBN 978-9939-1-1712-6.

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[1] Jampilek J. Heterocycles in Medicinal Chemistry. Molecules. 2019 Oct 25;24(21):3839. doi: 10.3390/molecules24213839. PMID: 31731387; PMCID: PMC6864827.

[2] Sharma PK, Amin A, Kumar M. A Review: Medicinally important nitrogen sulphur containing heterocycles. Open Med. Chem. J. 2020; 14:49-64.org/10.2174/1874104502014010049

[3] Kabir E, Uzzaman M. A review on biological and medicinal impact of heterocyclic compounds. Results in Chemistry. 2022; 4:100606. doi.org/10.1016/j.rechem.2022.100606

[4] Sharma V, Gupta M, Kumar P, Sharma A. A Comprehensive Review on Fused Heterocyclic as DNA Intercalators: Promising Anticancer Agents. Curr Pharm Des. 2021;27(1):15-42. doi: 10.2174/1381612826666201118113311. PMID: 33213325.

[5] Jubete G, de la Bellacasa PR, Estrada-Tejedor R, Teixido J, Borrell JI. Pyrido[2,3-d]pyrimidin-7(8H)-ones: synthesis and biomedical applications. Molecules. 2019; 24:4161. doi.org/10.3390/molecules24224161

[6] Tahlan S, Kumar S, Narasimhan B. Pharmacological significance of heterocyclic 1H-benzimidazole scaffolds: a review. BMC Chem. 2019 Aug 6;13(1):101. doi: 10.1186/s13065-019-0625-4. PMID: 31410412; PMCID: PMC6685272.

[7] Xiong H, Yu Q, Ma H, Yu X, Ouyang Y, Zhang ZM, Zhou W, Zhang Z, Cai Q. Exploration of tricyclic heterocycles as core structures for RIOK2 inhibitors. RSC Med Chem. 2023 Jul 21;14(10):2007-2011. doi: 10.1039/d3md00209h. PMID: 37859717; PMCID: PMC10583808.

[8] CA Chem. Substance Index. v.95, 6179CS. 1981.

[9] Hunter AD. ACD/ChemSketch 1.0 (freeware); ACD/ChemSketch 2.0 and its tautomers,dictionary, and 3D plug-ins; ACD/HNMR 2.0; ACD/CNMR 2.0. Chem. Educ. Easton.1997;74(8):905-908.

[10] Pyrimido[5’,4’:5,6]pyrido[1,2-a] Ger. Offen. Chem. Abstr. 1981; 95: P44732; 2.929. 414.

[11] Electrophotographic recording material. Wiedemann W. (Hoechst A.-G.). Ger. Offen. DE3.502.689, 33 pp. Chem. Abstr. 1987; 106:41561j.

[12] Electrophotographic recording material. Wiedemann W, Guenther D. (Hoechst A.-G.). Ger.Offen. Chem. Abstr. 1988; 108: DE 3.502.681;28:122003x.

[13] Bogdanowicz-Szwed K, Czarny A. Synthesis of polyazaheterocycles by Michael addition of CH acids to a α,β-unsaturated nitriles. Synthesis of pyrido[1,2-a]benzimidazole and pyrimido[5′,4' : 5,6]pyrido[l,2-a]benzimidazole derivatives. J. prakt. Chem. 1993; 335:279. org/10.1002/prac.19933350311

[14] Elwan NM. First synthesis of novel pentaheterocyclic ring system of 1,2,4-triazolo[2",3":6',1']pyrimido[4',5':2,3]pyrido[1,2-a] J. Heterocyclic Chem. 2004; 41:281. doi.org/10.1002/jhet.5570410222

[15] El-Zohry MF, Mohamed TA, Hussein EM. Novel syntheses of some new 3,4- dihydrospiro{benzimidazo[1,2-a]pyridine-3,30-indolin}-20-one derivatives. Monatsh. Chem. 2009; 140:265. org/10.1007/s00706-008-0013-6

[16] Harutyunyan AA. Synthesis of the derivatives of the new heterocyclic system 5,6-dihydrobenzo[4',5']imidazo[2',1':6,1]pyrido[2,3-d] Chem. J. Armenia. 2012; 65(2):257. https://arar.sci.am/publication/204311

[17] Harutyunyan АA, Panosyan HA, Tamazyan RA, Ayvazyan AG. New derivatives of the benzo[4,5]imidazo[2',1':6,1]pyrido[2,3-d] Chem. J. Armenia. 2016; 69(3):266. https://arar.sci.am/publication/205621

[18] Harutyunyan AA. Studies in the field of the pyrimidines and polycyclic azaheterocycles synthesis. The dissertation abstract of the doctor of chemical sciences. Armenia, Yerevan. 2017.

[19] Harutyunyan AA. Syntheses and biological properties of benzo[4', 5']imidazo[2',1': 6,1]-pyrido[2,3-d]pyrimidines: mini-review. Chem. J. Armenia. 2018; 71(4):579. https://arar.sci.am/publication/206351

[20] Harutyunyan AA, Gukasyan GT, Panosyan HA, Tamazyan RA, Ayvazyan AG, Grigoryan AG, Danagulyan GG. Synthesis of new derivatives of benzo[4',5']imidazo[2 ',1': 6,1]pyrido[2,3-d] Russ. J. Org. Chem. 2019; 55(11):1698. doi.org/10.1134/S1070428019110095

[21] Harutyunyan AA, Israelyan SG, Safaryan MS, Hakobyan MR, Sumbatyan AS, Dilanyan SV. Synthesis and biological properties of derivatives of five- and six-membered azaheterocycles and their condensed systems. Brief review of research by the laboratory for the synthesis of anti-cancer compounds in 2019-2023. Some Successes Organic and Pharmaceutical Chemistry. Collection of works. Issue 4, p. 112-135 (in English). Armenia, Yerevan. 2023; ISBN 978-9939-1-1712-6.