Novel cyanoacetamide integrated phenothiazines: Synthesis, characterization, computational studies and in vitro antioxidant and anticancer evaluations

Krishnan, Kannan Gokula; Kumar, C. Udhaya; Lim, Wei‐Meng; Wu, Chun; Veeraveedu, Punniyakoti T.; Ramalingan, Chennan

doi:10.1016/j.molstruc.2019.127037

Cited by 31 publications

(17 citation statements)

References 31 publications

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“…The aromatic and heteroaromatic C-H stretching bands are typically occurring below 3100 cm -1 [41,42]. In accordance with this, the absorption bands at 3031-3116 cm -1 in FT-IR spectrum and 3037-3245 cm -1 in FT-Raman spectrum are assigned to the C-H stretching frequency of the studied molecules.…”

Section: C-h Vibrationsupporting

confidence: 54%

Synthesis, spectral, crystallographic, and computational investigation of a novel molecular hybrid 3-(1-((benzoyloxy)imino)ethyl)-2H-chromen-2-ones

Krishnan¹,

Thanikachalam

2021

Eur J Chem

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Synthesis of 3-(1-((benzoyloxy)imino)ethyl)-2H-chromen-2-ones (1-5) was accomplished and it was characterized experimentally using various analytical techniques. Computational studies have been carried out for all compounds 1-5 using B3LYP method with 6-311++G(d,p) basis set. The optimized structural features viz. bond lengths, bond angles, and dihedral angles are compared with their single-crystal X-ray diffraction results of compound 1 (Crystal data for C18H13NO4 (M = 307.29 g/mol): Monoclinic, space group P21/c (no. 14), a = 11.399(5) Å, b = 5.876(5) Å, c = 21.859(5) Å, β = 91.060(5)°, V = 1463.9(14) Å3, Z = 4, T = 293(2) K, μ(MoKα) = 0.100 mm-1, Dcalc = 1.394 g/cm3, 13555 reflections measured (3.58° ≤ 2Θ ≤ 56.98°), 3669 unique (Rint = 0.0235) which were used in all calculations. The final R1 was 0.0444 (>2sigma(I)) and wR2 was 0.1506 (all data)), which are in good conformity with each other. Normal modes of vibrational frequencies of compounds 1-5 acquired from density-functional theory (DFT) method coincided with the experimental ones. The 1H and 13C chemical shifts of compounds 1-5 have been calculated by GIAO method and the results have been compared with the experimental ones. The first-order hyperpolarizability and their related properties of the novel molecules 1-5 are calculated computationally. The other parameters like natural bond orbital, zero-point vibrational energy, EHOMO, ELUMO, heat capacity and entropy have also been discussed.

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Section: C-h Vibrationsupporting

confidence: 54%

Synthesis, spectral, crystallographic, and computational investigation of a novel molecular hybrid 3-(1-((benzoyloxy)imino)ethyl)-2H-chromen-2-ones

Krishnan¹,

Thanikachalam

2021

Eur J Chem

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“…Additionally, by regulation of apoptosis-related proteins (Bcl-2, Bax, Bad, Parp, and DR5), 199 caused apoptosis induction against MCF-7 cells. 248 Very recently, Krishnan et al, 249 worked in the direction to accomplish the synthesis of phenothiazine based cyanoacrylamide analogs. These hybrids were assessed for in vitro anticancer evaluation against pancreatic tumor cells AsPC1 and SW1990.…”

Section: Phenothiazine and Azaphenothiazinementioning

confidence: 99%

“…Henceforth, the SAR established that there was a decline in the anticancer activity in order of ethyl < bromo substituted butyl < butyl < hexyl substitution (Figure 28). 249 F I G U R E 28 Phenothiazine derivatives as potential anticancer agents [Color figure can be viewed at wileyonlinelibrary.com]…”

Section: Phenothiazine and Azaphenothiazinementioning

confidence: 99%

Expedition of sulfur‐containing heterocyclic derivatives as cytotoxic agents in medicinal chemistry: A decade update

Laxmikeshav

Kumari

Shankaraiah

2021

Medicinal Research Reviews

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This review article proposes a comprehensive report of the design strategies engaged in the development of various sulfur-bearing cytotoxic agents. The outcomes of various studies depict that the sulfur heterocyclic framework is a fundamental structure in diverse synthetic analogs representing a myriad scope of therapeutic activities. A number of five-, six-and seven-membered sulfur-containing heterocyclic scaffolds, such as thiazoles, thiadiazoles, thiazolidinediones, thiophenes, thiopyrans, benzothiazoles, benzothiophenes, thienopyrimidines, simple and modified phenothiazines, and thiazepines have been discussed. The subsequent studies of the derivatives unveiled their cytotoxic effects through multiple mechanisms (viz. inhibition of tyrosine kinases, topoisomerase I and II, tubulin, COX, DNA synthesis, and PI3K/Akt and Raf/MEK/ERK signaling pathways), and several others. Thus, our concise illustration explains the design strategy and anticancer potential of these five-and six-membered sulfur-containing heterocyclic molecules along with a brief outline on seven-membered sulfur heterocycles. The thorough assessment of antiproliferative activities with the reference drug allows a proficient assessment of the structure-activity relationships (SARs) of the diversely synthesized molecules of the series.

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“…The modified phenothiazines exhibit not only anticancer activity, but a wide range of other activities such as the reversal of multidrug resistance, anti-inflammatory, antibacterial, antiviral, antiplasmid, cholinesterase inhibitory, antioxidant, and antihyperlipidemic and are considered potential agents in the treatment in Alzheimer’s and Creutzfeldt–Jakob diseases, published in hundreds of original papers and patents, and summarized in numerous comprehensive review papers and chapters [ 18 , 19 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 ].…”

Section: Introductionmentioning

confidence: 99%

Phenothiazines Modified with the Pyridine Ring as Promising Anticancer Agents

Morak‐Młodawska

Jeleń

Pluta

2021

Life

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Azaphenothiazines are the largest and most perspective group of modified phenothiazines, and they exhibit variety of biological activities. The review sums up the current knowledge on the anticancer activity of isomeric pyridobenzothiazines and dipyridothiazines, which are modified azaphenothiazines with one and two pyridine rings, respectively, against 10 types of cancer cell lines. Some 10-substituted dipyridothiazines and even 10-unsubstituted parent compounds, such as 10H-1,9-diazaphenothiazine and 10H-3,6-diazaphenothiazine, exhibited very potent action with the IC50 values less than 1 µg/mL and 1 µM against selected cancer cell lines. The strength of the anticancer action depends both on the tricyclic ring scaffolds and the substituents at the thiazine nitrogen atom. The review discusses the kind of the substituents, nature of tricyclic ring scaffolds with the location of the azine nitrogen atoms, the types of the cancer cell lines, and the mechanism of action.

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Novel cyanoacetamide integrated phenothiazines: Synthesis, characterization, computational studies and in vitro antioxidant and anticancer evaluations

Cited by 31 publications

References 31 publications

Synthesis, spectral, crystallographic, and computational investigation of a novel molecular hybrid 3-(1-((benzoyloxy)imino)ethyl)-2H-chromen-2-ones

Synthesis, spectral, crystallographic, and computational investigation of a novel molecular hybrid 3-(1-((benzoyloxy)imino)ethyl)-2H-chromen-2-ones

Expedition of sulfur‐containing heterocyclic derivatives as cytotoxic agents in medicinal chemistry: A decade update

Phenothiazines Modified with the Pyridine Ring as Promising Anticancer Agents

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