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BioMed Research International 2013Polyamines are substances involved in many aspects of cell growth, division, and differentiation. Because of the metabolic differences between host cells and parasite...
Polyamines are substances involved in many aspects of cell growth, division, and differentiation. Because of the metabolic differences between host cells and parasite cells, polyamine metabolism has been considered as a potential target for the chemotherapy of parasitic diseases. The aim of this work was to evaluate the schistosomicidal activity of different N-alkylated diamines (3a-3h), amino alcohols (4a-4d), and glycosylated amino alcohols (10a-10d). Compounds were prepared by synthetic methods and submitted to in vitro evaluation against adult worms of Schistosoma mansoni. At 100 μM, 3b, 3e, and 3h as well as 4a, 4b, 4d, 10a, 10b, and 10d resulted in 100% mortality of adult schistosomes. Compound 3d (12.5 to 100 μM) caused the death of 100% of both male and female adult schistosomes, while 3f (12.5 to 100 μM) resulted in 100% mortality of only male adult worms, whereas no mortality in female worms was observed. Compounds 3d and 3f were also able to reduce viability and decrease production of developed eggs in comparison with the negative control group. Diamines 3d and 3f may represent useful lead compounds for further optimization in order to develop new schistosomicidal agents.
Topics: Amino Alcohols; Animals; Diamines; Humans; Polyamines; Schistosoma mansoni; Schistosomiasis; Schistosomicides
PubMed: 24024211
DOI: 10.1155/2013/783490 -
Canadian Medical Association Journal May 1972
Topics: Amino Alcohols; Butanols; Drug Hypersensitivity; Humans; Oleic Acids; Otitis Externa; Peptides; Propylene Glycols
PubMed: 5032138
DOI: No ID Found -
British Medical Journal May 1972
Topics: Acetanilides; Adrenergic beta-Antagonists; Amino Alcohols; Arrhythmias, Cardiac; Drug Incompatibility; Humans; Verapamil
PubMed: 4401928
DOI: 10.1136/bmj.2.5810.405 -
British Medical Journal Dec 1970
Topics: Acetanilides; Adrenergic beta-Antagonists; Amino Alcohols; Heart; Humans; Hypertension; Propranolol; Respiration; Sympatholytics
PubMed: 4395725
DOI: 10.1136/bmj.4.5738.802-a -
British Medical Journal Dec 1970
Topics: Acetanilides; Adrenergic beta-Antagonists; Amino Alcohols; Animals; Cats; Guinea Pigs; Heart; Humans; Hypertension; Sympatholytics
PubMed: 4395276
DOI: 10.1136/bmj.4.5737.747 -
Memorias Do Instituto Oswaldo Cruz Aug 2009A series of diamines and amino alcohols derived from 1-dodecanol, 1-tetradecanol, 1,2-dodecanediol and 1,2-tetradecanediol were synthesized and tested for their...
A series of diamines and amino alcohols derived from 1-dodecanol, 1-tetradecanol, 1,2-dodecanediol and 1,2-tetradecanediol were synthesized and tested for their antitubercular activity. Compounds 3, 8 and 9 were found to be the most active (MIC of 6.25 microg/mL). Nine other compounds displayed activity against Mycobacterium tuberculosis, with a MIC of 12.5 microg/mL.
Topics: Amino Alcohols; Antitubercular Agents; Diamines; Microbial Sensitivity Tests; Mycobacterium tuberculosis
PubMed: 19820828
DOI: 10.1590/s0074-02762009000500006 -
Memorias Do Instituto Oswaldo Cruz Jun 2014Four diamines and three amino alcohols derived from 1-decanol, 1-dodecanol and 1,2-dodecanediol were evaluated in an in vitro assay against a mixture of trypomastigote...
Four diamines and three amino alcohols derived from 1-decanol, 1-dodecanol and 1,2-dodecanediol were evaluated in an in vitro assay against a mixture of trypomastigote and intracellular amastigote forms of Trypanosoma cruzi. Two of these compounds (6 and 7) showed better activity against both proliferative stages of T. cruzi than the positive control benznidazole, three were of similar potency (1, 2 and 5) and two were less active (3 and 4).
Topics: Amino Alcohols; Diamines; Dose-Response Relationship, Drug; Parasitic Sensitivity Tests; Trypanocidal Agents; Trypanosoma cruzi
PubMed: 24831550
DOI: 10.1590/0074-0276130496 -
Chirality Aug 2022New racemic vicinal amino alcohol derivatives with 4-benzylidenecyclohexane skeleton and axial chirality have been prepared. A preparatively easy and efficient protocol...
Synthesis, resolution, and absolute configuration determination of a vicinal amino alcohol with axial chirality. Application to the synthesis of new box and pybox ligands.
New racemic vicinal amino alcohol derivatives with 4-benzylidenecyclohexane skeleton and axial chirality have been prepared. A preparatively easy and efficient protocol for resolution of the N-benzoylamino alcohol is described. Using a 250 × 20 mm (L × ID) Chiralpak® IA column, and the appropriate mixture of n-hexane/ethanol/chloroform as eluent, both enantiomers of N-benzoylamino alcohol 3 are obtained with >99% enantiomeric excess (ee) by successive injections of a solution of the racemic sample in chloroform. The obtained axially chiral vicinal amino alcohol is used to synthesize structurally novel bisoxazoline ligands in high yields.
Topics: Amino Alcohols; Chloroform; Chromatography, High Pressure Liquid; Ethanol; Ligands; Stereoisomerism
PubMed: 35609966
DOI: 10.1002/chir.23475 -
TheScientificWorldJournal 2014A simple and efficient microwave-assisted methodology for the synthesis of 4-substituted-3-methyl-1,3-oxazolidin-2-ones from amino alcohols catalyzed by a ionic liquid...
A simple and efficient microwave-assisted methodology for the synthesis of 4-substituted-3-methyl-1,3-oxazolidin-2-ones from amino alcohols catalyzed by a ionic liquid was developed. This novel one-pot and one-step cyclization-methylation reaction represents an easier and faster method than any other reported protocols that can be used to obtain the desired products in good yields and high purity. Applying microwave irradiation at 130°C in the presence of TBAC, dimethyl carbonate acts simultaneously as carbonylating and methylating agent and surprisingly promotes an in situ basic trans esterification when a N-acetylated amino alcohol is used as starting material. Furthermore, dimethyl carbonate worked better than diethyl carbonate in performing this reaction.
Topics: Acetylation; Amino Alcohols; Chemistry Techniques, Synthetic; Formates; Methylation; Microwaves; Oxazolidinones
PubMed: 25692177
DOI: 10.1155/2014/634935 -
Molecules (Basel, Switzerland) Dec 2023A series of novel diterpene-type 1,3-aminoalcohols and their regioisomers have been synthesised from natural stevioside in a stereoselective manner. The key intermediate...
A series of novel diterpene-type 1,3-aminoalcohols and their regioisomers have been synthesised from natural stevioside in a stereoselective manner. The key intermediate β-keto alcohol was prepared using Wagner-Meerwein rearrangement of the epoxide derived from steviol methyl ester. The primary aminoalcohol was formed via Raney-nickel-catalysed hydrogenation of an oxime, and a versatile library of aminoalcohols was synthesised using a Schiff base with the primary amines. The aminoalcohol regioisomers were prepared from the mesylate of the β-keto alcohols. The corresponding primary aminoalcohol was formed via the palladium-catalysed hydrogenation of hydroxyl-azide, and click reactions of the latter were also carried out. The new compounds were characterised using 1D- and 2D-NMR techniques and HRMS measurements. The in vitro investigations showed high inhibition of cell growth in human cancer cell lines (HeLa, SiHa, A2780, MCF-7 and MDA-MB-231) in the case of naphthalic -substituted derivatives. The antiproliferative effects were assayed using the MTT method.
Topics: Female; Humans; Cell Line, Tumor; Ovarian Neoplasms; Amino Alcohols; HeLa Cells
PubMed: 38138451
DOI: 10.3390/molecules28247962