Synthesis of R(−)-3-Benzyl-5(Methoxycarbonyl-Methylthiomethyl)-Hydantoin, A Potential Chiral Intermediate for (+) Biotin

Ravindranathan, T.; Hiremath, S. V.; Ready, D. Rajgopal; Tejwani, R. B.

doi:10.1080/00397918808060941

Cited by 7 publications

(1 citation statement)

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“…Picolinyl and 4-chloropicolinyl chlorides were synthesized by the reactions of picolinic acid with SOCl 2 in the presence of Et 3 N and NaBr, respectively, and directly used in further steps without purification. Methyl S -benzyl- l -cysteinate, methyl S -allyl- l -cysteinate, and methyl S -(2-methoxy-2-oxoethyl)- l -cysteinate hydrochlorides were obtained from methyl l -cysteinate hydrochloride by a sequential treatment with Boc 2 O, the corresponding alkyl halide, and HCl. 2-Chloro- N -fluoresceinylacetamide used in the synthesis of ligand 12 was derived from 5-aminofluorescein and chloroacetyl chloride in the presence of sodium bicarbonate according to the published procedure .…”

Section: Experimental Sectionmentioning

confidence: 99%

Palladium(II) Pincer Complexes of Functionalized Amides with S-Modified Cysteine and Homocysteine Residues: Cytotoxic Activity and Different Aspects of Their Biological Effect on Living Cells

et al. 2021

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In the search for potential new metal-based antitumor agents, two series of nonclassical palladium(II) pincer complexes based on functionalized amides with S-modified cysteine and homocysteine residues have been prepared and fully characterized by 1D and 2D NMR ( 1 H, 13 C, COSY, HMQC or HSQC, 1 H− 13 C, and 1 H− 15 N HMBC) and IR spectroscopy and, in some cases, X-ray diffraction. Most of the resulting complexes exhibit a high level of cytotoxic activity against several human cancer cell lines, including colon (HCT116), breast (MCF7), and prostate (PC3) cancers. Some of the compounds under consideration are also efficient in both native and doxorubicin-resistant transformed breast cells HBL100, suggesting the prospects for the creation of therapeutic agents based on the related compounds that would be able to overcome drug resistance. An analysis of different aspects of their biological effects on living cells has revealed a remarkable ability of the S-modified derivatives to induce cell apoptosis and efficient cellular uptake of their fluorescein-conjugated counterpart, confirming the high anticancer potential of Pd(II) pincer complexes derived from functionalized amides with S-donor amino acid pendant arms.

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Section: Experimental Sectionmentioning

confidence: 99%

Palladium(II) Pincer Complexes of Functionalized Amides with S-Modified Cysteine and Homocysteine Residues: Cytotoxic Activity and Different Aspects of Their Biological Effect on Living Cells

et al. 2021

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Biotin

Outten¹

2000

Kirk-Othmer Encyclopedia of Chemical Technology

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Biotin is a water‐soluble B complex vitamin originally isolated from a variety of natural sources. In biological systems, biotin functions as a cofactor for enzymes involved in carboxylation reactions. A lack of biotin results in deficiency diseases in humans and animals. Daily intakes of biotin are recommended in the maintenance of optimal health. Several synthetic pathways to biotin have been developed since its stereochemical determination. The modern industrial synthesis is based on work done by researchers in the late 1940s. Since this work, industrial research has been directed toward process improvements in the basic methodology, particularly in the area of methods to form optically pure d ‐lactone. Research has also been directed toward elucidation of the biosynthetic pathway to biotin. Various microorganisms have been evaluated for use in biotin synthesis via fermentation. Recently, a number of patents have appeared on the synthesis of biotin using biotechnology. Several analytical methods, including microbiological, chemical, and chromatographic assays, are used to determine biotin levels in food and body fluids.

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Transition‐metal‐catalyzed reactions of 5‐methylene‐2‐oxazolidinone and 5‐methylene‐1,3‐thiazolidine‐2‐thione with isocyanates

Shen

Shi

2003

Applied Organom Chemis

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Synthesis of R(−)-3-Benzyl-5(Methoxycarbonyl-Methylthiomethyl)-Hydantoin, A Potential Chiral Intermediate for (+) Biotin

Cited by 7 publications

References 1 publication

Palladium(II) Pincer Complexes of Functionalized Amides with S-Modified Cysteine and Homocysteine Residues: Cytotoxic Activity and Different Aspects of Their Biological Effect on Living Cells

Palladium(II) Pincer Complexes of Functionalized Amides with S-Modified Cysteine and Homocysteine Residues: Cytotoxic Activity and Different Aspects of Their Biological Effect on Living Cells

Biotin

Transition‐metal‐catalyzed reactions of 5‐methylene‐2‐oxazolidinone and 5‐methylene‐1,3‐thiazolidine‐2‐thione with isocyanates

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