Carbonic anhydrase inhibition and cytotoxicity studies of Mannich base derivatives of thymol

Mannich bases of thymol were synthesized. The aminomethylation reaction was realised in the ortho position of the phenol for compounds 2 (dipropylamine), 3 (benzylamine), and 4 (dibenzylamine) while it was from para position for 1 (dimethylamine), 5 (piperidine), 6 (morpholine) and 7 (N-methylpipera...

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Published inJournal of enzyme inhibition and medicinal chemistry Vol. 31; no. 6; pp. 1375 - 1380
Main Authors Inci Gul, Halise, Yamali, Cem, Tugce Yasa, Asiye, Unluer, Elif, Sakagami, Hiroshi, Tanc, Muhammet, Supuran, Claudiu T.
Format Journal Article
LanguageEnglish
Published ABINGDON Taylor & Francis 01.11.2016
Subjects
Antineoplastic Agents - pharmacology
Biochemistry & Molecular Biology
Carbon-13 Magnetic Resonance Spectroscopy
Carbonic anhydrase
Carbonic Anhydrase Inhibitors - pharmacology
Carcinoma, Squamous Cell - pathology
Cell Line, Tumor
Chemistry, Medicinal
cytotoxicity
Drug Screening Assays, Antitumor
Humans
Life Sciences & Biomedicine
Mannich bases
Mannich Bases - chemistry
Mouth Neoplasms - pathology
Pharmacology & Pharmacy
phenol
Proton Magnetic Resonance Spectroscopy
Science & Technology
Spectrometry, Mass, Electrospray Ionization
thymol
Thymol - pharmacology
thymol
OXIDATIVE STRESS
ACID
Carbonic anhydrase
HYDROCHLORIDES
ANTICONVULSANT ACTIVITIES
phenol
Mannich bases
cytotoxicity
Online AccessGet full text

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Abstract Mannich bases of thymol were synthesized. The aminomethylation reaction was realised in the ortho position of the phenol for compounds 2 (dipropylamine), 3 (benzylamine), and 4 (dibenzylamine) while it was from para position for 1 (dimethylamine), 5 (piperidine), 6 (morpholine) and 7 (N-methylpiperazine). The carbonic anhydrase (CA, EC 4.2.1.1) inhibitory effects of the compounds were asssessed against hCA I and hCA II. All compounds moderately inhibited hCA I and hCA II. The cytotoxicity of the compounds against four human oral squamous cell carcinoma cell lines were compared those against three normal oral cells. Tumor specificity values were about 2 or slightly more for the compounds 2, 3, 4, 5 and 6. Compound 2 showed cytostatic activity against OSCC cell lines at 16 to 32-fold lower concentrations as compared with normal cells. This suggests that compound 2 can be considered as cytotoxicity enhancing drug candidate for further investigations.
AbstractList Mannich bases of thymol were synthesized. The aminomethylation reaction was realised in the ortho position of the phenol for compounds 2 (dipropylamine), 3 (benzylamine), and 4 (dibenzylamine) while it was from para position for 1 (dimethylamine), 5 (piperidine), 6 (morpholine) and 7 (N-methylpiperazine). The carbonic anhydrase (CA, EC 4.2.1.1) inhibitory effects of the compounds were asssessed against hCA I and hCA II. All compounds moderately inhibited hCA I and hCA II. The cytotoxicity of the compounds against four human oral squamous cell carcinoma cell lines were compared those against three normal oral cells. Tumor specificity values were about 2 or slightly more for the compounds 2, 3, 4, 5 and 6. Compound 2 showed cytostatic activity against OSCC cell lines at 16 to 32-fold lower concentrations as compared with normal cells. This suggests that compound 2 can be considered as cytotoxicity enhancing drug candidate for further investigations.
Author Inci Gul, Halise
Tanc, Muhammet
Tugce Yasa, Asiye
Sakagami, Hiroshi
Supuran, Claudiu T.
Yamali, Cem
Unluer, Elif
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Issue 6
Keywords thymol
OXIDATIVE STRESS
ACID
Carbonic anhydrase
HYDROCHLORIDES
ANTICONVULSANT ACTIVITIES
phenol
Mannich bases
cytotoxicity
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Snippet Mannich bases of thymol were synthesized. The aminomethylation reaction was realised in the ortho position of the phenol for compounds 2 (dipropylamine), 3...
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SubjectTerms Antineoplastic Agents - pharmacology
Biochemistry & Molecular Biology
Carbon-13 Magnetic Resonance Spectroscopy
Carbonic anhydrase
Carbonic Anhydrase Inhibitors - pharmacology
Carcinoma, Squamous Cell - pathology
Cell Line, Tumor
Chemistry, Medicinal
cytotoxicity
Drug Screening Assays, Antitumor
Humans
Life Sciences & Biomedicine
Mannich bases
Mannich Bases - chemistry
Mouth Neoplasms - pathology
Pharmacology & Pharmacy
phenol
Proton Magnetic Resonance Spectroscopy
Science & Technology
Spectrometry, Mass, Electrospray Ionization
thymol
Thymol - pharmacology
Title Carbonic anhydrase inhibition and cytotoxicity studies of Mannich base derivatives of thymol
URI https://www.tandfonline.com/doi/abs/10.3109/14756366.2016.1140755
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https://search.proquest.com/docview/1824546051
Volume 31
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