131357-77-2

Basic information

• Product Name: Benzamide, N-(4-oxo-4H-3,1-benzothiazin-2-yl)-
• CAS NO: 131357-77-2
• Molecular Formula: C15H10N2O2S
• Molecular Weight: 282.323
• Mol File: 131357-77-2.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: Benzamide, N-(4-oxo-4H-3,1-benzothiazin-2-yl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzamide, N-(4-oxo-4H-3,1-benzothiazin-2-yl)-(131357-77-2)
• EPA Substance Registry System: Benzamide, N-(4-oxo-4H-3,1-benzothiazin-2-yl)-(131357-77-2)

Safety Data

• Hazardous Substances Data: 131357-77-2(Hazardous Substances Data)

Upstream product

• 118-92-3 anthranilic acid 
• 532-55-8 Benzoyl isothiocyanate 
• 28144-70-9 anthranilic acid amide 
• 119118-95-5 N-benzoyl-N'-(2-cyanophenyl)thiourea 
• 13277-24-2 N-benzoyl-N'-(2-carboxyphenyl)thiourea 
• 131357-73-8 2-Amino-4-oxo-4H-3,1-benzothiazin 
• 93-97-0 benzoic acid anhydride 
• 115934-14-0 N-[[[2-(Aminocarbonyl)phenyl]amino]thioxomethyl)benzamide 

Downstream Products

• 13906-09-7 2-thioxo-2,3-dihydro-1H-quinazolin-4-one 
• 13277-24-2 N-benzoyl-N'-(2-carboxyphenyl)thiourea 

Relevant articles and documents

Polycyclic azines, XXV: 2-amino-3,1-benzothiazin-4-ones: Synthesis, Dimroth-Rearrangement to quinazolin-4(3H)-on-2(1H)-thiones, and MS/MS-fragmentation

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Benzothiazinones: A novel class of adenosine receptor antagonists structurally unrelated to xanthine and adenine derivatives

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 (Ki hA1 65.6 nM; hA2A 120 nM; hA2B 360 nM; hA 3 30.4 nM), while in rat (r), 10d was a highly potent A 1-selective antagonist (rA1 7.7 nM; rA2A 546 nM; rA2B 679 nM, rA3 >10000 nM). 2-(4- Methylbenzoylamino)-4H-3,1-benzothiazin-4-one (10g) was found to be a potent antagonist at human A2A (68.8 nM) and A3 ARs (23.0 nM) with high selectivity versus the other human AR subtypes. In contrast to A 1 and A3 ARs, A2A and A2B ARs tolerated bulky 2-acyl substituents. tert-Butyl (4-oxo-4H-3,1-benzothiazin-2- ylcarbamoyl)benzylcarbamate (15g, Ki hA2B 186 nM; hA 2A 603 nM) and 4-(4-benzylpiperazine-1-carbonyl)-N-(4-oxo-4H-3,1- benzothiazin-2-yl)benzamide (15k, hA2A 69.5 nM; hA2B 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.

Zur Bildung von 2-Amino-3,1-benzothiazin-4-on aus 2-(3-Benzoyl-thioureido)benzonitril

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