Refernces
10.1039/c6nj00782a
This study investigates the creation of sustainable epoxy monomers as alternatives to the diglycidyl ether of bisphenol A (DGEBA). The researchers synthesized diepoxydized diphenyls from eugenol, 4-vinyl guaiacol, and canolol through glycidylation with epichlorohydrin followed by cross metathesis (CM) dimerization using the Grubbs II catalyst. The synthesized products and their hydrolysed forms were then assessed for their potential endocrine-disrupting activity by estimating their binding affinity to the estrogen receptor a (ERa) using molecular docking. The study found that the epoxy forms had a moderate affinity to the antagonistic conformation of ERa, six to forty times lower than bisphenol A (BPA), while their hydrolysed forms exhibited relatively weak affinity in both agonistic and antagonistic conformations. This suggests that the synthesized bio-based epoxy monomers could serve as safer alternatives to DGEBA, with reduced potential for endocrine disruption.
10.1007/s00044-017-1805-1
Leishmaniasis, a tropical disease caused by Leishmania protozoa, is a significant public health concern with limited effective treatments. The study describes the synthesis of 21 1,3-bis(aryloxy)propan-2-amine derivatives from epichlorohydrin through a four-step process. Thiazolyl blue (MTT, 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) is a yellow water-soluble tetrazolium dye used in cell viability assays. MTT is used to assess the viability of L. amazonensis promastigotes and murine macrophages in the presence of the synthesized compounds. The study concludes that 1,3-bis(aryloxy)propan-2-amines have potential as antileishmanial agents, with the nature and position of aromatic ring substituents influencing their activity.
10.1248/cpb.50.1028
The study focuses on the development of a new synthetic route for the production of mono-O-protected anti-conformationally constrained pyrimidine acyclic nucleosides, which are potentially useful as antiviral and antitumoral agents, as well as tools in molecular biology. The researchers replaced 1,3-dibenzyloxypropan-2-ol with 1-benzyloxy-3(tert-butyldiphenylsilyloxy)propan-2-one (compound 4) as a key building block in the synthesis process. Various chemicals were utilized in this study, including epichlorohydrin, benzyl glycidyl ether, iodine, acetonitrile, water, tert-butylchlorodiphenylsilane, 4-N,N-dimethylaminopyridine (DMAP), pyridinium chlorochromate (PCC), n-butyllithium, tetrahydrofuran, and 2,4-dimethoxy-6-methylpyrimidine, among others. These chemicals served specific purposes in the synthesis process, such as acting as reagents, solvents, catalysts, or protecting groups, and were used in a series of reactions including ring-opening, silylation, oxidation, and dealkylation to achieve the desired nucleoside compounds with improved properties for applications in automated oligonucleotide synthesizers.
10.1016/j.molcata.2015.01.007
This research aimed to synthesize novel chiral polyethers derived from BINOL and ECH to serve as highly enantioselective and efficient catalysts for the borane reduction of prochiral ketones. The study focused on the asymmetric synthesis of enantiomerically enriched secondary alcohols, which are crucial synthetic intermediates in the pharmaceutical and agricultural industries. The researchers successfully synthesized two polyethers, Poly-5 and Poly-6, from BINOL and ECH, which were used to catalyze the reduction of prochiral ketones with borane, yielding secondary alcohols with up to 98% yields and over 99% enantiomeric excess (ee) values. The catalysts were found to be reusable without losing their enantioselective induction ability, making them a promising alternative for asymmetric synthesis. Key chemicals used in the process included 1,1-binaphthol (BINOL), epichlorohydrin (ECH), borane, and various ketones for the reduction reactions. The research concluded that the polyether Poly-6 was particularly efficient, offering high enantioselectivity and recyclability, and further development of other asymmetric reactions using these polyether ligands is ongoing.
10.1016/j.tetasy.2008.11.003
The research focuses on the chemoenzymatic synthesis of (2R,20S)-b-hydroxyhomometoprolol, a potential antihypertensive agent, aiming to improve upon previous synthetic methods by introducing an enzymatic resolution step for the efficient preparation of the oxirane precursor (R)-3. The study successfully developed a more efficient gram-scale synthesis method for the compound (R,S)-1, which showed significant antihypertensive and potential antiarrhythmic activity. The new approach eliminated the need for the previously reported fractional crystallization step, which was inefficient, and instead utilized the high enantioselectivity of Novozym 435 lipase for the resolution of racemic epoxide (±)2-((4-(2-methoxyethyl)phenoxy)methyl)oxirane rac-3. Key chemicals used in the process included 4-(2-methoxyethyl)phenol, epichlorohydrin, lithium chloride, acetic acid, vinyl stearate, and (S)-2-amino-1-butanol.
10.3906/kim-1005-607
The research investigates the asymmetric ring-opening of epichlorohydrin by salicylaldehyde derivatives using Co(III) salen catalysts. The study found that the ring-opening occurred at the phenolic groups most distant from the aldehydic group. Notably, switching catalysts led to a reversal in enantioselectivity. The addition of AlCl3 to the reaction mixture significantly accelerated the reaction rate without compromising product enantiopurity. Key chemicals involved in the research include epichlorohydrin, 2,3-dihydroxybenzaldehyde, 2,4-dihydroxybenzaldehyde, salicylaldehyde, Co(III) salen catalysts (1a and 1b), and AlCl3. The study also involved the synthesis of oximes and benzisoxazoles as part of the product characterization process.
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