ChemInform Abstract: One‐Step Synthesis of 2‐Aminothieno(2,3‐e)(1,3)thiazin‐4‐ones in Some Cases 5,6‐Anellated from Ethyl 2‐Benzoylthioureidothiophene‐3‐carboxylates and Evaluation of Their Antiallergic Activity.

Leistner, S.; Guetschow, Michael; Wagner, G.; Grupe, R; Boehme, B.

doi:10.1002/chin.198902215

Cited by 1 publication

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“…Treatment with isothiocyanates gave the thiourea derivatives 43 − 46 . Ring closure to 47 − 51 was then performed upon the action of concentrated sulfuric acid, according to previously reported procedures. , …”

Section: Resultsmentioning

confidence: 99%

“…Galanthamine hydrobromide was from Calbiochem (Bad Soden, Germany). Compounds 26 , 42 , 43 , 45 , 46 , 52 , 53 , 55 , 56 , 58 − 60 , 54 , 57 , and 61 − 63 38 were prepared as described elsewhere. All 1 H NMR and 13 C NMR data can be found in the Supporting Information.…”

Section: Methodsmentioning

confidence: 99%

“…2-Amino-7-benzyl-5,6,7,8-tetrahydro-4 H -pyrido[4 ‘ ,3 ‘ :4,5]thieno[2,3- d ][1,3]thiazin-4-one (47). Compound 47 was prepared from 43 as described, mp 161−163 °C …”

Section: Methodsmentioning

confidence: 99%

“…Ring closure to 47-51 was then performed upon the action of concentrated sulfuric acid, according to previously reported procedures. 76,77 Alkaline Hydrolysis. Stability of the compounds was measured spectrophotometrically in aqueous buffer, pH 11.0, at 25 °C.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of Tricyclic 1,3-Oxazin-4-ones and Kinetic Analysis of Cholesterol Esterase and Acetylcholinesterase Inhibition

Pietsch

Gütschow

2005

J. Med. Chem.

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A series of thieno[1,3]oxazin-4-ones and thieno[1,3]thiazin-4-ones were synthesized and investigated as inhibitors of the alpha/beta hydrolases cholesterol esterase (CEase) and acetylcholinesterase (AChE). The introduction of a cycloaliphatic five- or six-membered ring fused at the thiophene was favorable for CEase inhibition. Such compounds were analyzed as true alternate substrate inhibitors. 6,7-Dihydro-2-(dimethylamino)-4H,5H-cyclopenta[4,5]thieno[2,3-d][1,3]oxazin-4-one (33) exhibited a K(i) value of 630 nM and excelled in its low susceptibility to CEase-catalyzed degradation. Compound 33 and its analogues did not inhibit AChE. The introduction of a tetrahydropyrido ring with bulky hydrophobic substituents at the basic nitrogen provided inhibitors of AChE which were completely inactive toward CEase. 7-Benzyl-5,6,7,8-tetrahydro-2-(N-3,4-dimethoxybenzyl-N-methylamino)-4H-pyrido[4',3':4,5]thieno[2,3-d][1,3]oxazin-4-one (21) had the IC(50) value of 330 nM for AChE inhibition. A residual enzymatic activity at an infinite inhibitor concentration and thus a catalytically active ternary enzyme-substrate-inhibitor complex was concluded. To specify kinetic parameters of inhibition, a new method was derived to characterize selected thieno[1,3]oxazin-4-ones as hyperbolic mixed-type inhibitors of AChE.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

“…2-Amino-7-benzyl-5,6,7,8-tetrahydro-4 H -pyrido[4 ‘ ,3 ‘ :4,5]thieno[2,3- d ][1,3]thiazin-4-one (47). Compound 47 was prepared from 43 as described, mp 161−163 °C …”

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis of Tricyclic 1,3-Oxazin-4-ones and Kinetic Analysis of Cholesterol Esterase and Acetylcholinesterase Inhibition

Pietsch

Gütschow

2005

J. Med. Chem.

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“…1 H NMR (500 MHz, [D 6 ]DMSO): δ = 2.38 (s, 3H), 2.43 (s, 3H), 7.33 (d, J = 8.2 Hz, 2H), 7.57 (d, J = 8.3 Hz, 1H), 7.70 (dd, J = 8.3, 2.0 Hz, 1H), 7.85 (br s, 1H), 7.96 (d, J = 8.2 Hz, 2H), 12.12 (br s1H). 13 [2,3-d[1,3]thiazin-4-one (1.40 g, 66%), 44 mp 263−264 °C. A mixture of 2-amino-5,6-dimethyl-4Hthieno [2,3-d[1,3]thiazin-4-one (637 mg, 3 mmol), benzoic anhydride (1.36 g, 6 mmol), and toluene (25 mL) was refluxed for 2 h and kept at RT overnight.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Benzothiazinones: A Novel Class of Adenosine Receptor Antagonists Structurally Unrelated to Xanthine and Adenine Derivatives

et al. 2012

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2-(Acyl)amino-4H-3,1-benzothiazin-4-ones and related thienothiazinones were identified as structurally novel antagonists at adenosine receptors (ARs). 6-Methyl-2-benzoylamino-4H-3,1-benzothiazin-4-one (10d) was found to be a balanced AR antagonist with affinity for all human (h) subtypes (K(i) hA(1) 65.6 nM; hA(2A) 120 nM; hA(2B) 360 nM; hA(3) 30.4 nM), while in rat (r), 10d was a highly potent A(1)-selective antagonist (rA(1) 7.7 nM; rA(2A) 546 nM; rA(2B) 679 nM, rA(3) >10000 nM). 2-(4-Methylbenzoylamino)-4H-3,1-benzothiazin-4-one (10g) was found to be a potent antagonist at human A(2A) (68.8 nM) and A(3) ARs (23.0 nM) with high selectivity versus the other human AR subtypes. In contrast to A(1) and A(3) ARs, A(2A) and A(2B) ARs tolerated bulky 2-acyl substituents. tert-Butyl (4-oxo-4H-3,1-benzothiazin-2-ylcarbamoyl)benzylcarbamate (15g, K(i) hA(2B) 186 nM; hA(2A) 603 nM) and 4-(4-benzylpiperazine-1-carbonyl)-N-(4-oxo-4H-3,1-benzothiazin-2-yl)benzamide (15k, hA(2A) 69.5 nM; hA(2B) 178 nM) were highly selective versus the other AR subtypes. 2-Acylamino-3,1-benzothiazin-4-ones represent novel scaffolds suitable for the development of potent and selective AR antagonists for each of the four receptor subtypes.

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ChemInform Abstract: One‐Step Synthesis of 2‐Aminothieno(2,3‐e)(1,3)thiazin‐4‐ones in Some Cases 5,6‐Anellated from Ethyl 2‐Benzoylthioureidothiophene‐3‐carboxylates and Evaluation of Their Antiallergic Activity.

Abstract: ChemInform Abstract Reaction of the aminothiophenecarboxylates (I) with the isothiocyanate (II) yields the thioureas (III) which are cyclized under acidic conditions, forming the thienothiazines (IV). Their antiallergic activity is determined.

Cited by 1 publication

References 0 publications

Synthesis of Tricyclic 1,3-Oxazin-4-ones and Kinetic Analysis of Cholesterol Esterase and Acetylcholinesterase Inhibition

Synthesis of Tricyclic 1,3-Oxazin-4-ones and Kinetic Analysis of Cholesterol Esterase and Acetylcholinesterase Inhibition

Benzothiazinones: A Novel Class of Adenosine Receptor Antagonists Structurally Unrelated to Xanthine and Adenine Derivatives

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