Synthesis of thieno[2,3-b]quinoline and selenopheno[2,3-b]quinoline derivativesviaiodocyclization reaction and a DFT mechanistic study

Sonawane, Amol D.; Garud, Dinesh R.; Udagawa, Taro; Koketsu, Mamoru

doi:10.1039/c7ob02523h

Cited by 40 publications

(25 citation statements)

References 101 publications

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“…Structures of compounds 4a, [55] 4b, [56] 4c, [49] 4g, [49] and 4h [56] were confirmed by melting point as reported in literature. After the reaction completion, alkyl halide (0.01 mol) was added and stirred for further 1 h. The reaction mixture was poured into crushed ice and the precipitated solid obtained was filtered, washed with water, dried, and crystallized from methanol/water.…”

Section: General Procedures For the Synthesis Of 2-alkylthio-6-substsupporting

confidence: 81%

Novel quinoline derivatives carrying nitrones/oximes nitric oxide donors: Design, synthesis, antiproliferative and caspase-3 activation activities

Abdelbaset

Abdel‐Aziz

Abuo‐Rahma

et al. 2018

Arch. Pharm. Chem. Life Sci.

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Novel quinoline derivatives carrying nitrones and oxime as nitric oxide donors were prepared and characterized using different spectroscopic techniques. Nitrones can release nitric oxide in larger amounts compared to corresponding oximes. Antiproliferative screening results showed that the 2-benzylthioquinoline nitrones 6e and 6f and the 2-methylthio analogues 6g and 6h exhibited promising antiproliferative activity especially against leukemia and colon cancer cell lines. Compounds 6c, 6e, and 6f exhibited higher potency as anticancer agents compared to doxorubicin, with IC 50 ranging from 0.45 to 0.91 μM. A remarkable overexpression of caspase-3 protein levels was observed in cells treated with the tested compounds. Compound 6e exhibited more pre-G1 apoptosis and cell cycle arrest at the G2/M phase than in other phases.These results revealed that the tested compounds can cause programmed cell death through overexpression of caspase 3, which may be attributed to the release of nitric oxide. K E Y W O R D S antiproliferative, apoptosis, caspase 3, nitric oxide, nitrones, oximes 1 | INTRODUCTION Quinoline is a significant nucleus which has attracted the attention of medicinal chemists due to its variable pharmacological activities. Easy functionalization of various ring positions of quinoline makes it an attractive synthetic building block for design and synthesis of new drugs. Additionally, quinolines are considered as an interesting group of compounds, many of which have widespread pharmacologicalactions such as anti-microbial, [1][2][3][4] anti-inflammatory, [5][6][7][8] antitubercular, [9][10][11][12] anti-convulsant, [13] antihypertensive, [14,15] antioxidant, [16][17][18][19] and anticancer [20] activities. Several mechanisms can explain the anticancer effect of quinoline derivatives including: topoisomerase inhibition, [21][22][23] DNA intercalation, [24] protein kinases inhibition, [25][26][27] tubulin polymerase inhibition, [28][29][30][31] and induction of apoptosis. [32,33] Quinoline derivative I exhibited potent anticancer activity against brain cancer cell line U87 with IC 50 of 1.5 nM. [31] Compound II exhibits remarkable anticancer activity against HL60 cancer cell line with IC 50 of 0.68 μM (Figure 1). [33] Incorporation of biologically active moieties into quinoline such as nitrones [34] and oximes [35] may produce biologically active anticancer agents.Compound III showed significant anticancer activity with IC 50 of 31.42 μM against Hep-G 2 cancer cell line (Figure 1). [34] Nitrones are a Arch Pharm Chem Life Sci. 2019;352:e1800270.wileyonlinelibrary.com/journal/ardp

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Section: General Procedures For the Synthesis Of 2-alkylthio-6-substsupporting

confidence: 81%

Novel quinoline derivatives carrying nitrones/oximes nitric oxide donors: Design, synthesis, antiproliferative and caspase-3 activation activities

Abdelbaset

Abdel‐Aziz

Abuo‐Rahma

et al. 2018

Arch. Pharm. Chem. Life Sci.

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“…The regioselective iodocyclization reaction of 3alkynyl-2-(methylseleno)quinolines 168 was carried out for the synthesis of selenopheno[2,3-b]quinoline 169 derivatives via iodocyclization reaction (Scheme 61). [106] Electrophilic-cyclization reaction of the 2-alkynylbenzyl selenide derivatives 172 using iodine as an electrophilic source gave 4-iodo-3-substituted 1Hisoselenochromenes 173 in moderate yields. The cyclization followed 6-endo-dig mode (Scheme 62).…”

Section: Synthesis Of Selenated Quinoline Isoselenochromene and Pyramentioning

confidence: 99%

Synthesis of Seleno‐Heterocycles via Electrophilic/Radical Cyclization of Alkyne Containing Heteroatoms

Sonawane

Ninomiya

et al. 2020

Adv Synth Catal

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containing heterocyclic scaffolds by virtue of their interesting reactivities and a broad range of applications in the medicinal and materials chemistry. This review involves the electrophilic/radical cyclization of alkynes containing heteroatoms which resulted into the novel Se‐heterocycles. The synthesis of seleno‐heterocycles via different nucleophiles including O, N, S, Se, Te, and C‐nucleophiles is exhaustively discussed. Also, one‐pot electrophilic cyclization of 1,3‐diynes and 1,3,5‐triynes was described in details. Furthermore, the various mechanisms underlying the synthesis of selenium‐β‐lactam, carbapenem heterocycle, bis‐ and tris‐selenide alkene, β‐selenosulfonation and selenated alkynes were discussed. The Se‐heterocycles reported in this review allow preparing these selenated compounds bearing the selenium moiety both on the rings (outside) and inside the ring (e. g. selenophenes). The review demonstrates the growing opportunities to construct selenium containing heterocycles from alkynes containing heteroatoms.

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“…The carbon atom attached to CF 3 is more electrophilic because of the highly electronegative nature of CF 3 group, which in turn is susceptible to a nucleophilic attack by the hydroxyl ion to the intermediate CVIII. In 2018, the synthesis of selenopheno[2,3-b]quinoline 146 through the iodo-cyclization reaction of 3-alkynyl-2-(methylseleno)quinolines 145 in DCM at room temperature for 6 h, using I2 or NIS as an electrophilic source, was reported [179]. Under these reaction conditions, the corresponding fused selenophenes 146a and 146b were synthetized in 54% and 75% yields, respectively, by the iodocyclization of 3-alkynyl-2-(methylseleno)quinolines 145a (R = H) and 145b (R = Br), using Niodosuccinimide (NIS) as an electrophilic source.…”

Section: Starting From Type C Precursormentioning

confidence: 99%

Recent Advances in the Synthesis of Selenophenes and Their Derivatives

et al. 2020

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The selenophene derivatives are an important class of selenium-based heterocyclics. These compounds play an important role in prospecting new drugs, as well as in the development of new light-emitting materials. During the last years, several methods have been emerging to access the selenophene scaffold, employing a diversity of cyclization-based synthetic strategies, involving specific reaction partners and particularities. This review presents a comprehensive discussion on the recent advances in the synthesis of selenophene-based compounds, starting from different precursors, highlighting the main differences, the advantages, and limitations among them.

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Synthesis of thieno[2,3-b]quinoline and selenopheno[2,3-b]quinoline derivativesviaiodocyclization reaction and a DFT mechanistic study

Cited by 40 publications

References 101 publications

Novel quinoline derivatives carrying nitrones/oximes nitric oxide donors: Design, synthesis, antiproliferative and caspase-3 activation activities

Novel quinoline derivatives carrying nitrones/oximes nitric oxide donors: Design, synthesis, antiproliferative and caspase-3 activation activities

Synthesis of Seleno‐Heterocycles via Electrophilic/Radical Cyclization of Alkyne Containing Heteroatoms

Recent Advances in the Synthesis of Selenophenes and Their Derivatives

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