Novel pyrazolo[3,4-d]pyrimidines as potential anticancer agents: Synthesis, VEGFR-2 inhibition, and mechanisms of action

Ruzi, Zukela; Bozorov, Khurshed; Nie, Liping; Zhao, Jiaheng; Aisa, Haji Akber

doi:10.1016/j.biopha.2022.113948

Cited by 15 publications

(15 citation statements)

References 78 publications

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“…Interestingly, among the arylidenes, ( E )‐9‐(3,4‐dimethoxybenzylidene)‐2‐(4‐fluorophenyl)‐6,7,8,9‐tetrahydro‐4 H ‐furo[2,3‐ d ]pyrido[1,2‐ a ]pyrimidin‐4‐one ( 8c ) was a selective sample only against HeLa cell lines with an IC 50 value of 8.46±0.43 μM. It should be noted that substituents of the benzylidene fragments in the furo[2,3‐ d ]pyrimidine system contain only the methoxy (−OMe) group, and this can be explained by our previous research advances [54] . Recently, we have discovered a novel pyrazolo[3,4‐d]pyrimidines bearing aryl(heteryl)idene moiety as potential anticancer agents, [54] which by SAR analysis ( Figure 4) suggests the importance of methoxy group in the antiproliferative activity toward the human cancer cell lines.…”

Section: Resultsmentioning

confidence: 85%

“…Interestingly, among the arylidenes, (E)-9- It should be noted that substituents of the benzylidene fragments in the furo[2,3-d]pyrimidine system contain only the methoxy (À OMe) group, and this can be explained by our previous research advances. [54] Recently, we have discovered a novel pyrazolo [3,4-d]pyrimidines bearing aryl(heteryl)idene moiety as potential anticancer agents, [54] which by SAR analysis (Figure 4) suggests the importance of methoxy group in the antiproliferative activity toward the human cancer cell lines.…”

Section: In Vitro Antiproliferative Activity and Structure -Activity ...mentioning

confidence: 99%

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Furo[2,3‐d]pyrimidines as Mackinazolinone/Isaindigotone Analogs: Synthesis, Modification, Antitumor Activity, and Molecular Docking Study

Song

Nie

Bozorov

et al. 2023

Chemistry & Biodiversity

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The chemical transformation of the tricyclic furo[2,3‐d]pyrimidines was performed under isosteric and scaffold‐hopping strategies focusing on the synthesis of its arylidene and imine‐containing derivatives. Naturally‐occurring alkaloids mackinazolinone and isaindigotone were as templates of target heterocycles. Synthesized compounds evaluated for their antitumor activity on human cancer cervical HeLa, breast MCF‐7, and colon HT‐29 cell lines. Four compounds: 8c, 8e, 10b, and 10c demonstrated potency against HeLa and HT‐29 cell lines, and IC50 values were between 7.37–13.72 μM, respectively. The molecular docking results showed that compounds 8c and 10b had good binding and high matching with the target EGFR protein.

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Section: Resultsmentioning

confidence: 85%

Section: In Vitro Antiproliferative Activity and Structure -Activity ...mentioning

confidence: 99%

Furo[2,3‐d]pyrimidines as Mackinazolinone/Isaindigotone Analogs: Synthesis, Modification, Antitumor Activity, and Molecular Docking Study

Song

Nie

Bozorov

et al. 2023

Chemistry & Biodiversity

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“…2-Amino-4-asetonil-5-izopropiltiofen-3-karbon kislotasi nitrilini (6) chumoli yoki sirka kislotada 6 soat qizdirilganda tegishli 2-N(metil)-tiyeno [2,3-d]pirimidin-4-onlar (7) hosil bo'ladi [29]: R=H, CH 3 2-Aminotiofen-3-karbon kislota amidlari (8,9) formamid bilan kondensasiyalanganda 70% unum bilan tegishli tiyeno [2,3-d]pirimidin-4-onlar (10,11) hosil bo'lgan. Olingan mahsulotlar (10,11) metansulfonilxlorid (MsCl) yoki benzolsulfonilxloridlar bilan piridinda o'zaro ta'sirlashganda tegishli metil- (12) yoki fenilsulfonatlar (13) olingan [30]:…”

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“…Введение. Хиназолиновые алкалоиды широко распространены в растениях [1,2], используемых в народной медицине [3][4][5][6][7][8]. В последние годы в фармакологии перспективным классом соединений признаны тиофеновые аналоги хиназолиновых алкалоидов [9,10].…”

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Xinazolin Alkaloidlarining Tiofenli Analoglari: 2-N(alkil, Aril)-Tieno[2,3-D]pirimidinonlarning Sintezi Va Modifikasiyasi

Asqarov¹,

Aisa²,

Bozorov³

et al. 2022

ЖурХимТовНарМед

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Xinazolin alkaloidlari xalq tabobatida qo’llaniladigan o’simliklar tarkibida keng uchraydi. So’nggi yillarda, farmakologiyada xinazolin alkaloidlarining tiofenli analoglari istiqbolli sinf birikmalari sifatida e’tirof etilmoqda. Mazkur sharhli maqola xinazolin alkaloidlarining tiofenli analoglari, jumladan 2-alkil- va aril tiyeno[2,3-d]pirimidinonlar sintezi va ularning transformasiyasiga bag’ishlangan.

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Current scenario of fused pyrimidines with in vivo anticancer therapeutic potential

Xu,

Wang,

2024

Archiv der Pharmazie

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Cancer, characterized by uncontrolled cell growth and metastasis, is responsible for nearly one in six deaths and represents a severe threat to public health worldwide. Chemotherapy can substantially improve the quality of life and survival of patients with cancer, but anticancer chemotherapeutics are associated with a range of adverse effects. Moreover, almost all currently available anticancer chemotherapeutics could develop drug resistance over a period of time of application in cancer patients and ultimately lead to cancer relapse and death in 90% of patients, creating an urgent need to develop new anticancer agents. Fused pyrimidines trait the inextricable part of DNA and RNA and are vital in numerous biological processes. Fused pyrimidines can act on various biological cancer targets and have the potential to address drug resistance. In addition, more than 20 fused pyrimidines have already been approved for clinical treatment of different cancers and occupy a prominent place in the current therapeutic arsenal, revealing that fused pyrimidines are privileged scaffolds for the development of novel anticancer chemotherapeutics. The purpose of this review is to summarize the current scenario of fused pyrimidines with in vivo anticancer therapeutic potential along with their acute toxicity, metabolic profiles as well as pharmacokinetic properties, toxicity and mechanisms of action developed from 2020 to the present to facilitate further rational exploitation of more effective candidates.

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Novel pyrazolo[3,4-d]pyrimidines as potential anticancer agents: Synthesis, VEGFR-2 inhibition, and mechanisms of action

Cited by 15 publications

References 78 publications

Furo[2,3‐d]pyrimidines as Mackinazolinone/Isaindigotone Analogs: Synthesis, Modification, Antitumor Activity, and Molecular Docking Study

Furo[2,3‐d]pyrimidines as Mackinazolinone/Isaindigotone Analogs: Synthesis, Modification, Antitumor Activity, and Molecular Docking Study

Xinazolin Alkaloidlarining Tiofenli Analoglari: 2-N(alkil, Aril)-Tieno[2,3-D]pirimidinonlarning Sintezi Va Modifikasiyasi

Current scenario of fused pyrimidines with in vivo anticancer therapeutic potential

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