Vitamin B6 derivatives. 13. Synthesis of tetrahydrothiazine derivatives of vitamin B6 and their biological properties

Okumura, Kentaro; Oda, T.; Kondo, Kazuyoshi; Inoue, Ichizo; Danno, Tamotsu; Yamaguchi, H.; Masukawa, Kenji

doi:10.1021/jm00285a012

Cited by 12 publications

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“…1) was prepared by the method of Okumuru et at. [12]. Oleoyl HCT amide (II) was prepared by stirring 10.0 g of oleoyl chloride [15] with 5.10 g of HCT hydrochloride at 80 °C until the solution was achieved.…”

Section: Methodsmentioning

confidence: 99%

Homocysteine Compounds which Influence the Growth of a Malignant Neoplasm

McCully¹,

Clopath²

1977

Chemotherapy

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Since homocysteine metabolism is important in the control of normal and abnormal growth, three homocysteine derivatives were synthesized and tested for effects on the growth of transplanted murine adenocarcinoma. Arachidonoyl homocysteine thiolactone (HCT) amide decreased growth, and oleoyl HCT amide increased growth of the neoplasm. Pyridoxal HCT enamine decreased the growth of the neoplasm when given for 2 weeks prior to transplantation, but the compound had no effect when given after transplantation. The two inhibitory substances were tolerated well by normal mice except in high doses. These findings suggest an approach to prevention and therapy of human malignancy which utilizes homocysteine derivatives of normal biochemical constituents.

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Section: Methodsmentioning

confidence: 99%

Homocysteine Compounds which Influence the Growth of a Malignant Neoplasm

McCully¹,

Clopath²

1977

Chemotherapy

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“…[Fe(Gly) 2 ] [59] (crystal structure:S upporting Information, Figure S21), S-N,N'-{[2-(methylthio)ethyl]ethylene}bis(salicyliden-imine) (salmetH 2 ), 2-amino-5-thiahexylamine (= S-methionamine, Supporting Information, compound C8 in Scheme S2) [60] and homocysteineamide hydrochloride [61,62] (Supporting Information, compound C3 in Scheme S1) were synthesized according to literature procedures. S-(5'-adenosyl)-l-methionine p-toluene sulfonate (SAM-pTs , % 90 %), S-(5'-adenosyl)-l-methionine iodide (SAM-I, > = 80 %), and S-(5'-adenosyl)-l-methionine chloride dihydrochloride (SAM-Cl*2 HCl, > = 75 %) were commercially available at Sigma-Aldrich.…”

Section: Selectedsynthetic Proceduresmentioning

confidence: 99%

“…Water was degassed by three freeze-pump-thaw cycles. [Fe(Gly) 2 ] [59] (crystal structure:S upporting Information, Figure S21), S-N,N'-{ [2-(methylthio)ethyl]ethylene}bis(salicyliden-imine) (salmetH 2 ), 2-amino-5-thiahexylamine (= S-methionamine, Supporting Information, compound C8 in Scheme S2) [60] and homocysteineamide hydrochloride [61,62] (Supporting Information, compound C3 in Scheme S1) were synthesized according to literature procedures. The labels C1-C10 refer to compound names in Scheme S1 and Scheme S2 depicted in the Supporting Information.…”

Section: Selectedsynthetic Proceduresmentioning

confidence: 99%

Alkyl Radical Generation by an Intramolecular Homolytic Substitution Reaction between Iron(II) and Trialkylsulfonium Groups

Jungen

Chen

2018

Chemistry A European J

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Intramolecular, homolytic substitution reactions between iron(II) species and various trialkylsulfonium groups were directly observed in the gas phase upon collision-induced dissociation. In spite of the notoriously low reduction potential of trialkylsulfonium species and the mismatched oxidation potential of iron(II), the reactions proceed at moderate collision energies, forming an alkyl radical as well as a thioether coordinated to the iron. In contrast to classical homolytic substitutions, the attacking radical is a "metalloradical", namely iron(II) that is oxidized to iron(III) during the reaction. With this process we demonstrate that the conceptually analogous, putative radical generation step in radical S-adenosyl methionine (SAM) enzymes is possible and plausible. Further, we show that this kind of reaction only occurs in constrained systems with a defined geometry. Combining experimental measurements with DFT studies and NBO analyses allowed us to gain insights into the reactivity and transition states of these systems. Based on our findings, we challenge the notion of a collinear transition state in the radical generation step of radical SAM enzymes and propose it to be bent instead.

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“…Amidation reactions are most frequently used: conjugation with acid halides [80][81][82][83], (in situ) activated carboxylic acids [83][84][85][86][87][88][89], and anhydrides [90] enables the synthesis of homocysteine-γ-thiolactone derivatives. A carbamate linkage is formed by treatment with chloroformates [91]. An important homocysteine-γ-thiolactone derivative is N-acetylhomocysteinethiolactone or citiolone 2 (Scheme 2), a commercial compound that was introduced as a thiolating agent for proteins.…”

Section: Reactivity and Synthetic Use Of Homocysteine-γ-thiolactone Amentioning

confidence: 99%

One-Pot Double Modification of Polymers Based on Thiolactone Chemistry

Espeel

Prez

2014

Multi-Component and Sequential Reactions in Polymer Synthesis

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One-pot multistep reactions based on thiolactone chemistry have emerged as a powerful tool for modifying thiolactone-containing polymers in one-pot and in an elegant manner. In general, thiolactones can be opened by a wide variety of functional amines and the released thiol can react with thiol 'scavengers' of choice. This overview highlights the most important features of this approach, illustrated by the versatile and site-specific double postpolymerization modification of various reactive systems.

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Vitamin B6 derivatives. 13. Synthesis of tetrahydrothiazine derivatives of vitamin B6 and their biological properties

Cited by 12 publications

References 0 publications

Homocysteine Compounds which Influence the Growth of a Malignant Neoplasm

Homocysteine Compounds which Influence the Growth of a Malignant Neoplasm

Alkyl Radical Generation by an Intramolecular Homolytic Substitution Reaction between Iron(II) and Trialkylsulfonium Groups

One-Pot Double Modification of Polymers Based on Thiolactone Chemistry

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