613. Isothiazole: a new mononuclear heterocyclic system

Adams, Anna; Slack, Robert J.

doi:10.1039/jr9590003061

Cited by 63 publications

(20 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…101 (g) Reductive desulphurisation of isothiazole derivatives. 102 (h) Amidomethylation of aryl acetic esters. 103 (i) Amidomethylation of monosubstituted malonic-or cyanoacetic esters.…”

Section: Enantioselective Synthesis Of ␤ 2 -Amino Acids Via Chiral ␤-mentioning

confidence: 99%

β²‐amino acids—syntheses, occurrence in natural products, and components of β‐peptides^1,2

2004

View full text Add to dashboard Cite

Although they are less abundant than their alpha-analogues, beta-amino acids occur in nature both in free form and bound to peptides. Oligomers composed exclusively of beta-amino acids (so-called beta-peptides) might be the most thoroughly investigated peptidomimetics. Beside the facts that they are stable to metabolism, exhibit slow microbial degradation, and are inherently stable to proteases and peptidases, they fold into well-ordered secondary structures consisting of helices, turns, and sheets. In this respect, the most intriguing effects have been observed when beta2-amino acids are present in the beta-peptide backbone. This review gives an overview of the occurrence and importance of beta2-amino acids in nature, placing emphasis on the metabolic pathways of beta-aminoisobutyric acid (beta-Aib) and the appearance of beta2-amino acids as secondary metabolites or as components of more complex natural products, such as peptides, depsipeptides, lactones, and alkaloids. In addition, a compilation of the syntheses of both achiral and chiral beta2-amino acids is presented. While there are numerous routes to achiral beta2-amino acids, their EPC synthesis is currently the subject of many investigations. These include the diastereoselective alkylation and Mannich-type reactions of cyclic- or acyclic beta-homoglycine derivatives containing chiral auxiliaries, the Curtius degradation, the employment of transition-metal catalyzed reactions such as enantioselective hydrogenations, reductions, C-H insertions, and Michael-type additions, and the resolution of rac. beta2-amino acids, as well as several miscellaneous methods. In the last part of the review, the importance of beta2-amino acids in the formation of beta-peptide secondary structures is discussed.

show abstract

“…101 (g) Reductive desulphurisation of isothiazole derivatives. 102 (h) Amidomethylation of aryl acetic esters. 103 (i) Amidomethylation of monosubstituted malonic-or cyanoacetic esters.…”

Section: Enantioselective Synthesis Of ␤ 2 -Amino Acids Via Chiral ␤-mentioning

confidence: 99%

β²‐amino acids—syntheses, occurrence in natural products, and components of β‐peptides^1,2

2004

View full text Add to dashboard Cite

show abstract

“…This carbon, known to be highly electrophilic, [48][49][50] was a probable site for initial attack by hydrazine and as such both steric and electronic factors that influence the C-5 position could affect the ring transformation. To investigate this, a series of 3-chloro-5-substituted isothiazole-4-carbonitriles bearing steric and/or electronic constraints at C-5 were treated with anhydrous hydrazine to examine their effect on reaction time and pyrazole yields ( Table 3).…”

Section: Modification Of Substituents At C-5mentioning

confidence: 99%

“…Initially hydrazine could attack the highly electrophilic isothiazole C-5 carbon [48][49][50] to afford the 2,5-dihydroisothiazole 71 that could be in equilibrium with its ring opened form 72. When R 1 was a good leaving group (e.g., R 1 ¼Cl), loss of R 1 H and sulfur could give the hydrazinyl acrylonitrile 73.…”

Section: Mechanistic Rationalementioning

confidence: 99%

The conversion of isothiazoles into pyrazoles using hydrazine

Ioannidou

Koutentis

2009

Tetrahedron

View full text Add to dashboard Cite

“…This compound and some of its derivatives were first described by Adams and Slack (1959) and its antibacterial properties were reported by Adams and others (1960).…”

Section: -~-Aminobenzen~ulphonamido-~-~hylisothiazole (I)mentioning

confidence: 95%

“…179-180", were prepared by acetylating the corresponding amines in sodium carbonate solution with acetic anhydride (cf. Adams and Slack, 1959). …”

mentioning

confidence: 95%

The Metabolism of 5-p-Aminobenzenesulphonamido-3-Methylisothiazole (Sulphasomizole)

Bridges

1963

Journal of Pharmacy and Pharmacology

View full text Add to dashboard Cite

The fate of the sulphonamide drug, sulphasomizole, in man, dog, rabbit and rat has been studied. In man, rat and rabbit, the major urinary metabolite, is N4-acetylsulphasomizole together with the unchanged drug. In man about 60 per cent of an oral dose of 30 mg./kg. is excreted in the urine in 24 hr., just over a third being acetylated. In the rabbit about 80 per cent of an oral dose (150 mg./kg. is excreted in 24 hr. and about two-thirds is acetylated. In the rat about 70 per cent of the dose (150 mg./kg.) is excreted in 24 hr. and just under one third is acetylated. In the dog, the main excretory product is the unchanged drug, there being no acetylation. All four species excrete small amounts (1 per cent) of the N4-glucuronide of sulphasomizole. Other minor metabolites detected were the N4-sulphate of sulphasomizole which was found in rat and dog urine, and an unidentified oxidation product present as a glucuronide which was detected in rabbit and dog urine. 5-~-AMINOBENZEN~ULPHONAMIDO-~-~HYLISOTHIAZOLE (I)is an antibacterial drug containing a new heterocyclic system, namely the isothiazole or 1,2-thiazole ring system. This compound and some of its derivatives were first described by Adams and Slack (1959) and its antibacterial properties were reported by Adams and others (1960). Me __ IThe compound is marketed as a sulphonamide drug of moderateThe substance has duration of action under the name of "Bidizole". been given the approved common name, sulphasomizole. EXPERIMENTAL MaterialsSulphasomizole, m.p. 189", 5-p-aminobenzenesulphonacetamido-3-methylisothiazole (W-acetylsulphasomizole), m.p. 168-169", 5-amino-3-methylisothiazole, m.p. 41-42", 4-amino-3-hydroxybenenesulphonic acid, m.p. 266" (decomp.) and 4-amino-2-hydroxybenzenesulphonic acid were the gifts of May & Baker, Ltd., Dagenham, Essex. 5-p-Acetamidobenzenesulphonamido-3-methylisothiazole (N4-acetylsulphasomizole), m.p. 272-273" and 5-acetamid0-3-methylisothiazole, m.p. 179-180", were prepared by acetylating the corresponding amines in sodium carbonate solution with acetic anhydride (cf. Adams and Slack, 1959). 565

show abstract

613. Isothiazole: a new mononuclear heterocyclic system

Cited by 63 publications

References 0 publications

β²‐amino acids—syntheses, occurrence in natural products, and components of β‐peptides^1,2

β²‐amino acids—syntheses, occurrence in natural products, and components of β‐peptides^1,2

The conversion of isothiazoles into pyrazoles using hydrazine

The Metabolism of 5-p-Aminobenzenesulphonamido-3-Methylisothiazole (Sulphasomizole)

Contact Info

Product

Resources

About

613. Isothiazole: a new mononuclear heterocyclic system

Cited by 63 publications

References 0 publications

β2‐amino acids—syntheses, occurrence in natural products, and components of β‐peptides1,2

β2‐amino acids—syntheses, occurrence in natural products, and components of β‐peptides1,2

The conversion of isothiazoles into pyrazoles using hydrazine

The Metabolism of 5-p-Aminobenzenesulphonamido-3-Methylisothiazole (Sulphasomizole)

Contact Info

Product

Resources

About

β²‐amino acids—syntheses, occurrence in natural products, and components of β‐peptides^1,2

β²‐amino acids—syntheses, occurrence in natural products, and components of β‐peptides^1,2