3-(Hydroxymethyl)pyridine - CAS 100-55-0
Not Intended for Therapeutic Use. For research use only.
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3-Pyridinemethanol, an aromatic alcohol compound, is a widely used in the synthesis of some inhibitors like Chk1 and histone deacetylase inhibitors.
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Chemical Structure
CAS 100-55-0 3-(Hydroxymethyl)pyridine

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Reference Reading

1.An Efficient Strategy for Self-Assembly of DNA-Mimic Homochiral 1D Helical Cu(II) Chain from Achiral Flexible Ligand by Spontaneous Resolution.
Zhang X1, Li B1, Zhang J1. Inorg Chem. 2016 Apr 4;55(7):3378-83. doi: 10.1021/acs.inorgchem.5b02785. Epub 2016 Mar 21.
Four helical copper complexes Cu[N(CN)2]2(Hhmp) (1), {Cu[N(CN)2]2(Hhmp)}∞ (2), (l-{Cu4[N(CN)2]2(hmp)4(CH3COO)2·CH3CN}∞ (3a), and d-{Cu4[N(CN)2]2(hmp)4(CH3COO)2·CH3CN}∞ (3b) (Hhmp = 2-(hydroxymethyl)pyridine) have been prepared toward a mimic DNA structure. By changing the solvent and supplementary ligand, the structures can be successfully tuned from quasi-double-helical (complex 1) to racemic 1D single helix (complex 2), then the right (3a)-/left (3b)-handed double helices. The topologies of 3a and 3b may be considered as a mimic of DNA, where the Cu-O bonds between the two strands replace the hydrogen-bonding interactions in DNA. Solid-state circular dichroism spectra confirmed that 3a and 3b are optically active, respectively. Magnetic measurements for 1-3 indicated all complexes to be antiferromagnetic interactions. The best fitting results to the magnetic susceptibilities were J = -0.80 cm(-1), g = 2.11 for 1 and J1 = -9.22 cm(-1), J2 = 3.
2.Antibacterial Activity and Cytotoxicity of Silver(I) Complexes of Pyridine and (Benz)Imidazole Derivatives. X-ray Crystal Structure of [Ag(2,6-di(CH₂OH)py)₂]NO₃.
Kalinowska-Lis U1, Felczak A2, Chęcińska L3, Szabłowska-Gadomska I4, Patyna E5, Małecki M6, Lisowska K7, Ochocki J8. Molecules. 2016 Jan 28;21(2). pii: E87. doi: 10.3390/molecules21020087.
Selected aspects of the biological activity of a series of six nitrate silver(I) complexes with pyridine and (benz)imidazole derivatives were investigated. The present study evaluated the antibacterial activities of the complexes against three Gram-negative strains: Pseudomonas aeruginosa ATCC 15442, Escherichia coli ATCC 25922 and Proteus hauseri ATCC 13315. The results were compared with those of silver nitrate, a silver sulfadiazine drug and appropriate ligands. The most significant antibacterial properties were exerted by silver(I) complexes containing benzimidazole derivatives. The cytotoxic activity of the complexes was examined against B16 (murine melanoma) and 10T1/2 (murine fibroblasts) cells. All of the tested silver(I) compounds were not toxic to fibroblast cells in concentration inhibited cancer cell (B16) viability by 50%, which ranged between 2.44-28.65 µM. The molecular and crystal structure of silver(I) complex of 2,6-di(hydroxymethyl)pyridine was determined by single-crystal X-ray diffraction analysis.
3.In vitro anti-Giardia lamblia activity of 2-aryl-3-hydroxymethyl imidazo[1,2-a]pyridines and -pyrimidines, individually and in combination with albendazole.
Velázquez-Olvera S1, Salgado-Zamora H2, Jiménez-Cardoso E3, Campos-Aldrete ME4, Pérez-González C5, Ben Hadda T6. Acta Trop. 2016 Mar;155:6-10. doi: 10.1016/j.actatropica.2015.11.013. Epub 2015 Dec 3.
Giardiasis is a major diarrheal disease found throughout the world, the causative agent being the flagellate protozoan Giardia intestinalis. Infection is more common in children than in adults. The appearance of drug resistance has complicated the treatment of several parasitic diseases, including giardiasis. Thus, the aim of this investigation was to make an in vitro evaluation of the antigiardia response of synthetic derivatives 2-aryl-3-hydroxymethylimidazo[1,2-a]pyridines 1 and -pyrimidines 2 against trophozoites of Giardia lamblia WB, in comparison with the reference drug, albendazole. Additionally, the synergistic action of albendazole in combination with each of the most active 2-aryl-3-hydroxymethyl imidazo[1,2-a]pyridines and pyrimidines was also assessed. Based on the IC50 values obtained, the best anti-Giardia activity was provided by the 3-hydroxymethyl-4-fluorophenylimidazo[1,2-a]pyrimidine derivative 2c and the corresponding imidazo[1,2-a]pyrimidine with the p-tolyl substituent 2d, followed by 2a and 2b.
4.Caffeine Cytochrome P450 1A2 Metabolic Phenotype Does Not Predict the Metabolism of Heterocyclic Aromatic Amines in Humans.
Turesky RJ1, White KK2, Wilkens LR2, Le Marchand L2. Chem Res Toxicol. 2015 Aug 17;28(8):1603-15. doi: 10.1021/acs.chemrestox.5b00177. Epub 2015 Aug 6.
2-Amino-1-methylimidazo[4,5-b]pyridine (PhIP) and 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx) are carcinogenic heterocyclic aromatic amines (HAAs) formed in well-done cooked meats. Chemicals that induce cytochrome P450 (P450) 1A2, a major enzyme involved in the bioactivation of HAAs, also form in cooked meat. Therefore, well-done cooked meat may pose an increase in cancer risk because it contains both inducers of P450 1A2 and procarcinogenic HAAs. We examined the influence of components in meat to modulate P450 1A2 activity and the metabolism of PhIP and MeIQx in volunteers during a 4 week feeding study of well-done cooked beef. The mean P450 1A2 activity, assessed by caffeine metabolic phenotyping, ranged from 6.3 to 7.1 before the feeding study commenced and from 9.6 to 10.4 during the meat feeding period: the difference in means was significant (P < 0.001). Unaltered PhIP, MeIQx, and their P450 1A2 metabolites, N(2)-(β-1-glucosiduronyl)-2-(hydroxyamino)-1-methyl-6-phenylimidazo[4,5-b]pyridine (HON-PhIP-N(2)-Gl); N3-(β-1-glucosiduronyl)-2-(hydroxyamino)-1-methyl-6-phenylimidazo[4,5-b]pyridine (HON-PhIP-N3-Gl); 2-amino-3-methylimidazo-[4,5-f]quinoxaline-8-carboxylic acid (IQx-8-COOH); and 2-amino-8-(hydroxymethyl)-3-methylimidazo[4,5-f]quinoxaline (8-CH2OH-IQx) were measured in urine during days 2, 14, and 28 of the meat diet.