Spectroscopic investigation, fungicidal activity and molecular dynamics simulation on benzimidazol-2-yl carbamate derivatives

Mol, G.P. Sheeja; Aruldhas, D.; Joe, I. Hubert; Balachandran, S.; Anuf, A. Ronaldo; George, Jesby

doi:10.1016/j.molstruc.2018.08.092

Cited by 14 publications

(4 citation statements)

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“…Compounds 5-9 and with amino or mercapto group in the position 5 of 1,3-oxazole ring have been shown to exhibit moderate anticancer activity ranging from 67.29 (for compound 7, NCI-H522 of non-small cell lung cancer) to 131.64 (for compound 9, OVCAR-3 of ovarian cancer). Compound 13 was active against leukemia: CCRF-CEM (−10,68), K-562 (54,67), MOLT-4 (−6,82); colon cancer: SW-620 (54,03); melanoma: LOX IMVI (38,89).…”

Section: In Vitro Evaluation Of the Anticancer Activitymentioning

confidence: 99%

“…Compound 14 was active against leukemia: CCRF-CEM (−13,84), HL-60(TB) (36,09), K-562 (1,85), MOLT-4 (−36,39), SR (−27,66); non-small cell lung cancer: NCI-H522 (−82,02); colon cancer: HCT-116 (0,21), SW-620 (−37,71); melanoma: LOX IMVI (7,99), MALME-3M (−47,84), M14 (38,39); renal cancer: ACHN (24,37), TK-10 (−25,29); breast cancer: T-47D (3,98). Compounds 12, 14-16, 19, and 20 satisfied the predetermined threshold inhibition criteria of the NCI-60…”

Section: -Arylsulfonylmentioning

confidence: 99%

“…[10] Among the molecular characteristics to be used for structure-pharmacological activity relationship, the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) energies have been shown to correlate particularly well with various biological activities. [36][37][38][39][40][41][42] It is to be taken into account that biological activity or generation of the stable "rigid" structure with the receptors depends on the chemical constitution of target, including its possible electron structure.…”

Section: Introductionmentioning

confidence: 99%

“…Among the molecular characteristics to be used for structure‐pharmacological activity relationship, the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) energies have been shown to correlate particularly well with various biological activities …”

Section: Introductionmentioning

confidence: 99%

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Dependence of the anticancer activity of 1,3‐oxazole derivatives on the donor/acceptor nature of his substitues

Kachaeva

Hodyna

Obernikhina

et al. 2019

Journal of Heterocyclic Chem

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A series of new 1,3‐oxazole derivatives, containing in position 5 both donor and acceptor substituents were synthesized. These substances were considered as potentially active anticancer pharmacophores in the human tumor cell line panel derived from nine cancer types, including lung, colon, melanoma, renal, ovarian, brain, leukemia, breast, and prostate. Primary in vitro one‐dose anticancer screening was shown that compounds with acceptor substituents (such as –C(O)OMe, –CN) in the position 5 inhibit the growth of most cell lines, and compounds with donor substituents (such as –NHR, −SR) in the position 5 do not practically inhibit the growth of cancer cell lines. It can be assumed that the pharmacological activity of 1,3‐oxazole derivatives depends on donor/acceptor nature of the substituents in position 5. It was proposed to evaluate the donor/acceptor ability of 1,3‐oxazole derivatives using the special parameter φ0, which takes into account the relative position of the boundary levels (HOMO end LUMO). The quantum‐chemical modeling was performed; the special parameter φ0 for 1,3‐oxazole derivatives correlates with the experimental results. Quantum‐chemical calculations of the special parameter φ0 allow modeling the pharmacological activity of 1,3‐oxazole derivatives by introducing donor or acceptor substituents at position 2 or 5. This work may be useful for chemists to develop a target synthesis of potential biologically active compounds.

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Section: In Vitro Evaluation Of the Anticancer Activitymentioning

confidence: 99%