Synthesis and antiplatelet, antiinflammatory, and antiallergic activities of substituted 3-chloro-5,8-dimethoxy-1,4-naphthoquinone and related compounds

Huang, Li Jiau; Chang, Fu Chaio; Lee, Kuo Hsiung̀; Wang, Jih Pyang; Teng, Che-Ming; Kuo, Sheng Chu

doi:10.1016/s0968-0896(98)80006-0

Cited by 46 publications

(21 citation statements)

References 9 publications

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“…In 1 H NMR spectra of 6, the presence of benzoquinone proton was confirmed by one signal at δ 5.19 ppm (s). And, in 13 C NMR spectrum of 6, two quinonic carbonyl moieties (C=O) appeared in δ 176.8 and 176.3 ppm, as expected. In the mass spectra (ESI-MS) of this compound (6), the protonated [M+H] + molecular ion peak gave m/z= 451.3 in the positive ion mode and molecular ion peak gave m/z [M] -=449.5 in the negative ion mode, which were agreement with the molecular formula.…”

Section: Resultssupporting

confidence: 77%

“…And, these compounds are important in many fields including medicinal chemistry, color chemistry, optical data storage, photoconductors, supercapacitors, coordination polymers (4)(5)(6)(7)(8)(9)(10). Especially, these compounds are of particular interest because of their biological and chemotherapeutic activities, such as antifungal, antibacterial, anti-tumor, antiinflammatory, antiplatelet, and antiallergic (11)(12)(13). The biological activity of the quinones is related to the redox chemistry of these compounds (14)(15).…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of Some Mono-, Bis- NH-substituted-1,4-Benzoquinones

Kaçmaz¹

2018

Journal of the Turkish Chemical Society Section A: Chemistry

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The preparation of new mono-and bis-NH-substituted-1,4-benzoquinones, namely 2,5bis (5,6-dimethylbenzo[d]thiazol-2-ylamino)cyclohexa-2,5-diene-1,4-dione (3), 2,5-bis(3-(2methylpiperidin-1-yl)propylamino)-3-chlorocyclohexa-2,5-diene-1,4-dione (6), 2-(4-tertbutylbenzylamino)-3,5,6-trichlorocyclohexa-2,5-diene-1,4-dione (9), 2-(4-fluorophenylamino)-6tert-butylcyclohexa-2,5-diene-1,4-dione (12) are reported. The synthesis of new quinone derivatives (3, 6, 9, 12) have been carried out from the reactions between quinones (pbenzoquinone (1), 2,6-dichloro-1,4-benzoquinone (4), tetrachloro-1,4-benzoquinone (7) or 2-tertbutyl-1,4-benzoquinone (10)) and different amines (2-amino-5,6-dimethylbenzothiazole (2), N-(3aminopropyl)-2-pipecoline (5), 4-tert-butylbenzylamine (8) or 4-fluoroaniline (11)). The new compounds were characterized by elemental analysis, mass spectrometry, IR, 1 H-NMR, 13 C-NMR spectroscopy.Cite this: Kaçmaz A. Synthesis of Some Mono-, Bis-NH-substituted-1,4-Benzoquinones. JOTCSA. 2018;5(2):963-70.

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Section: Resultssupporting

confidence: 77%

Section: Introductionmentioning

confidence: 99%

Synthesis of Some Mono-, Bis- NH-substituted-1,4-Benzoquinones

Kaçmaz¹

2018

Journal of the Turkish Chemical Society Section A: Chemistry

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“…The existence of one Cl atom in 5d,e was confirmed by mass spectrometry. We then treated 2,3-dichloro-5,8-dihydroxy-1,4-naphthoquinone [21] (6f) with 9-AA in refluxing EtOH [Route (a)] to afford reddish crude product 5f in 93 % yield. This product was of sufficient purity that no further purification was necessary.…”

Section: Synthesis Of 9-(acridinylamino)quinone Derivatives 5a-f By Amentioning

confidence: 99%

One‐Pot Synthesis of Novel Antiproliferative 9‐Aminoacridines

et al. 2011

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“…In addition, the quinone moiety can also serve as an electrophile and can react with different biological targets in various species including human. 1,4-Naphthoquinones are reported to have a variety of pharmacological properties, including antibacterial, 1 antifungal, 2,3 antiviral, 4–6 anti-inflammatory, 7,8 antiartherosclerotic, 9 and anticancer effects. 10–12 …”

Section: Introductionmentioning

confidence: 99%

Anticancer activity and SAR studies of substituted 1,4-naphthoquinones

Bhasin

Chettiar

Etter

et al. 2013

Bioorganic & Medicinal Chemistry

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In this paper, we report the structure–activity relationship studies of substituted 1,4-naphthoquinones for its anticancer properties. 1,4-Naphthoquinone, Juglone, Menadione, Plumbagin and LLL12.1 were used as lead molecules to design PD compounds. Most of the PD compounds showed improved antiproliferative activity in comparison to the lead molecule in prostate (DU-145), breast (MDA-MB-231) and colon (HT-29) cancer cell lines. PD9, PD10, PD11, PD13, PD14 and PD15 were found to be the most potent compound with an IC50 value of 1–3 μM in all cancer cell lines. Fluorescent polarization assay was employed to study the inhibition of STAT3 dimerization by PD compounds. PD9 and PD18 were found to be potent STAT3 dimerization inhibitors.

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Synthesis and antiplatelet, antiinflammatory, and antiallergic activities of substituted 3-chloro-5,8-dimethoxy-1,4-naphthoquinone and related compounds

Cited by 46 publications

References 9 publications

Synthesis of Some Mono-, Bis- NH-substituted-1,4-Benzoquinones

Synthesis of Some Mono-, Bis- NH-substituted-1,4-Benzoquinones

One‐Pot Synthesis of Novel Antiproliferative 9‐Aminoacridines

Anticancer activity and SAR studies of substituted 1,4-naphthoquinones

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