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Chromanone-A Prerogative Therapeutic Scaffold: an Overview

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Chromanone-A Prerogative Therapeutic Scaffold: an Overview Arabian Journal for Science and Engineering https://doi.org/10.1007/s13369-021-05858-3 REVIEW-CHEMISTRY Chromanone‑A Prerogative Therapeutic Scafold: An Overview Sonia Kamboj1,2 · Randhir Singh1 Received: 28 September 2020 / Accepted: 9 June 2021 © King Fahd University of Petroleum & Minerals 2021 Abstract Chromanone or Chroman-4-one is the most important and interesting heterobicyclic compound and acts as a building block in medicinal chemistry for isolation, designing and synthesis of novel lead compounds. Structurally, absence of a double bond in chromanone between C-2 and C-3 shows a minor diference from chromone but exhibits signifcant variations in biological activities. In the present review, various studies published on synthesis, pharmacological evaluation on chroman- 4-one analogues are addressed to signify the importance of chromanone as a versatile scafold exhibiting a wide range of pharmacological activities. But, due to poor yield in the case of chemical synthesis and expensive isolation procedure from natural compounds, more studies are required to provide the most efective and cost-efective methods to synthesize novel chromanone analogs to give leads to chemistry community. Considering the versatility of chromanone, this review is designed to impart comprehensive, critical and authoritative information about chromanone template in drug designing and development. Keywords Chroman-4-one · Chromone · Pharmacological activity · Synthesis · Analogues 1 Introduction dihydropyran (ring B) which relates to chromane, chromene, chromone and chromenone, but the absence of C2-C3 dou- Chroman-4-one is one of the most important heterobicyclic ble bond of chroman-4-one skeleton makes a minor difer- moieties existing in natural compounds as polyphenols and ence (Table 1) from chromone and associated with diverse as synthetic compounds like Taxifolin, also known as chro- biological activities [1]. manone or benzo-dihydropyran or benzopyran. Structurally, chroman-4-one is a fusion of benzene nucleus (ring A) with * Randhir Singh [email protected] 1 Maharishi Markandeshwar College of Pharmacy, Maharishi Markandeshwar (Deemed to be University), Mullana, Haryana 133203, India 2 Ch. Devi Lal College of Pharmacy, Jagadhri, Haryana 135003, India Vol.:(0123456789)1 3 Arabian Journal for Science and Engineering O O 4 4 4 4 3 3 3 3 2 2 2 O 2 O O O 1 1 1 1 Chromane Chromene Chroman -4-one Chromone Natural and synthetic chromanone analogs show vari- other diseases [4]. Presently, a number of research groups ous biological activities such as anticancer, tumor necrosis are working in designing and development of more potent factor-α (TNF-α) inhibitors, antivascular, antidiabetic, anti- and signifcant chromanone analogues. So, in the present oxidant, antimicrobial, antifungal, antiviral, antileishmanial, review, recent literature available up to 2020 about chro- insecticidal, spasmolytic, analgesic, anti-infammatory, anti- man-4-one derivative and their pharmacological activities coagulant, estrogenic inhibitor, anti-acetylcholinesterase is accrued. Present review article will ofer a platform to the (AchE) inhibitor, antihuman immunodefciency virus (HIV), researchers in designing and development of novel potent anticonvulsant, antidepressants, anticoronal and antituber- chroman-4-one analogs. cular activity. Due to of these activities, several analogues of chromane are also available in market like tocopherols 2 Biological Activities of Chromanone (vitamin E), taxifolin (antidiabetic), tetrazole (antidiabetic), troglitazone (antidiabetic), ormeloxifene (anticancer) and 2.1 Anticancer Activity nebivolol (beta-blocker) [2]. Moreover, several isolated fa- vanones, favonols, homoisofavonoids like naringenin, nar- ingin, myricetin, dihydroquercetin and kaempferol are also Discovery and development of novel anticancer agents under clinical studies [3]. Therefore, among the diverse array with potent cytotoxic activity is one of the top priorities in of chromane, chroman-4-one/4-chromanone are of consider- pharmaceutical research. Several limitations like variable able interest to researchers due to potency of this clinically efcacy, poor toxicity profle and adverse efects are associ- useful pharmacophore in the treatment of cancer and several ated with the usage of currently available chemotherapeutic agents [5]. Generally, cancer can be measured by assessing Table 1 Properties of chromanone and chromone Name Chroman-4-one Chromone IUPAC name 4-Chromanone 4-Chromone Other names (Synonym) Chromanone, 4-chromanone, chroman-4-one dihydrobenzo pyran, Chromone, 4-Chromone, benzopyran, 2,3-dihydro-4H-1-benzopyran-4-one 4H-Chromen-4-one,4H-1-Benzo- pyran-4-one Structure O O 4 4 3 3 2 2 O O 1 1 Formula C9H8O2 C9H6O2 Formula weight 148.15 g/mol 146.14 g/mol Molecular weight 148.15 g/mol 146.14 g/mol Density 1.196 ± 0.06 g/cm3 1.248 ± 0.06 g/cm3 Xlog P3 1.4 ± 0.24 1.4 ± 0.24 Melting point 36.5 ºC 59.0 ºC Composition 72.96% 73.97% C 5.44% 4.14% H 21.60% 21.90% O 1 3 Arabian Journal for Science and Engineering OH OH OH OH H3CO O HO O HO O OH O OH O OH O Naringenin Eriodictoyl Sakuranetin OH OH OH OCH3 OCH3 H3CO HO O O H HO O O O OO H CH3 OH O Sterubin Deguellin CH3 Hesperetin Fig. 1 Natural favanones containing chroman-4-one as parent moiety O O O O HO O HO O OH OH 4-hydroxyflavonone 5,4'-Dideoxyflavonone 5-Dideoxyflavonone OH OH OH OCH3 OH HO O HO O H3CO O OH OH O OH O OH O Hesperetin (2S,3S)-trans-Dihydroquercetin Sakuranetin Fig. 2 Chroman-4-one derived structure (under development phase) the degree of mitochondrial impairment and metabolic dys- in lipid metabolism and unbalanced pH [6]. Therefore, to functions such as cellular energy supply, cell death signal- cure such metabolic dysfunctions, naturally occurring fa- ing, irregulation of metabolic pathways, formation of reac- vonoids, favonols, favanones (2-phenyl chroman-4-one tive oxygen species (ROS), compromised enzyme actions, derivatives) and homoisofavanones exhibit good anticancer aerobic glycolysis augmented in tumor cells, alterations potential along with other pharmacological activities such 1 3 Table 2 Chroman-4-one analogs exhibiting anticancer activity Sr. No. Compound Structure Evaluation Inference 1 (E)-3-benzylidene-7-methoxychroman-4-one O Evaluated against MDA-MB-231 (breast Signifcant inhibition against MDA- derivatives (3-chloro-4,5-dimethoxyben- Cl cancer), KB (nasopharyngeal epidermoid MB-231 = 7.56 ± 2.23, KB = 25.04 ± 10.60 zylidene derivative) carcinoma) and SK-N-MC (human neuro- and SK-N-MC = 9.64 ± 2.7 blastoma) cell lines using MTT assay Marked as best anticancer agent among the H3CO O OCH3 series [16] OCH3 2 (E)-3-(2′-methoxybenzylidene)-4-chromanone OOCH 3 Evaluated for antiproliferative activity in Exhibited highest potency against proliferation HUVEC (human umbilical vein endothelial of endothelial cells with IC50 = 19 µM [17] cells) O 3 6,7-Methylenedioxy-4-chromanone O Evaluated against three breast cancer cell lines Exhibited highest anticancer activity against (MCF-7, T47D and MDA-MB-231) tested cell lines (IC ≤ 9.3 µg/ml) [18] O 50 O O 4 3-Benzylidene-chroman-4-one derivatives O Evaluated against K562, MDA-MB-231 and Exhibited potent anticancer activity with OCH 3 SK-N-M Cell lines IC50 ≤ 3.86 µg/ml [19] HO O OH Br 5 Hydroxy favanones O Evaluated against colorectal carcinoma cells Exhibited potent cytotoxic activity [20] OH such as A549, LLC, AGS, SK-Hepl and HA22T cancer cells O O OH ScienceandEngineering Journalfor Arabian O Cl 6 Synthetic favanones (4′,7-dimethoxyfa- O Evaluated for antiproliferative activity against Exhibited potent cytotoxic activity [21] vanone) MCF-7 (human breast cancer) cells Apoptotic cell population = 34.89% H3CO O OCH3 1 3 Arabian Journal for ScienceandEngineering Journalfor Arabian Table 2 (continued) Sr. No. Compound Structure Evaluation Inference O 7 Halogenated favanones 3′,7-dichlorofavanone Evaluated against MCF-7, LNCaP, PC3, Hep- Very potent compound (IC50 = 2.9 µM) against G2, KB, SK-N-MC cells MDA-MB-231 cell line than etoposide (refer- ence drug) [22] Cl Cl O 3′,6-Dichlorofavanone O Cl Cl O O 8 7, 8-Methylenedioxyfavanones Examine cytotoxic potential and apoptosis in Exhibit better cytotoxic potency than reference human leukemia cells [23] O O R1 O R1=2'-Cl or 2'-NO2 OH O 9 2’-Chloro- or 2′-nitro-substituted chroman- Tested for cytotoxic activity against Bel-7402, Showed signifcant cytotoxic activity [24] H3C 4-one compounds HL-60, BGC-823 and KB (human cancer HO O R1 cell lines) CH3 R1=2'-Cl or 2'-NO2 10 7-Methoxyisofavanone O Evaluated against HL60 (acute myeloblastic Displayed highest anticancer activity against leukemia cells) and PBMC (peripheral blood HL60 cells [25] mononuclear cells) using MTT assay H3CO O Diarylchromanone O H3CO O NO 2 11 3-Arylidenefavanone and chromanone (E, Z Screened against HL-60, NALM-6, WM115 Z-isomer (chromanone) was found to be more isomers) and 3-arylfavones O and normal cells HUVEC cancer cell lines cytotoxic, while E-isomer was entirely inac- tive IC50 = 0.9 ± 0.2 (HL60), H N 1.6 ± 0.3 (NALM-6), O 6.3 ± 0.5 (WM-115), 5.77 ± 0.17(HUVEC) [26] 1 3 Table 2 (continued) Sr. No. Compound Structure Evaluation Inference OOH 12 3-Benzylchroman-4-ones Examined against two cancerous cell lines 3-Benzylchroman-4-one derivatives (a) BT549 (human breast carcinoma), HeLa was found to be the most active against O (human cervical carcinoma) and one BT549 (IC50 = 20.1 mM), HeLa cell lines (a) noncancerous cell line Vero (normal kidney (IC50 = 42.8 mM), whereas 3-benzylchroman- epithelial cells)
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