195986-91-5

Basic information

• Product Name: 5-HYDROXY ISATOIC ANHYDRIDE
• Synonyms: 6-HYDROXY-1H-BENZO[D][1,3]OXAZINE-2,4-DIONE;5-HYDROXY ISATOIC ANHYDRIDE;6-Hydroxy-2H-3,1-benzoxazine-2,4(1H)-dione;2H-3,1-Benzoxazine-2,4(1H)-dione, 6-hydroxy-;6-Hydroxy-2H-3,1-benzoxazine-2,4(1H)-dione, 6-Hydroxy-1H-benzo[d][1,3]oxazine-2,4-dione;6-Hydroxyisatoic anhydride;6-hydroxy-2H-benzo[d][1,3]oxazine-2,4(1H)-dione
• CAS NO: 195986-91-5
• Molecular Formula: C₈H₅NO₄
• Molecular Weight: 179.13
• Mol File: 195986-91-5.mol

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.56g/cm³
• Refractive Index: 1.631
• PKA: 8.82±0.20(Predicted)
• CAS DataBase Reference: 5-HYDROXY ISATOIC ANHYDRIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-HYDROXY ISATOIC ANHYDRIDE(195986-91-5)
• EPA Substance Registry System: 5-HYDROXY ISATOIC ANHYDRIDE(195986-91-5)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 195986-91-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-Hydroxy isatoic anhydride is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to form a range of biologically active compounds, contributing to the development of new drugs and therapeutic agents.
Used in Agrochemical Industry:
In the agrochemical sector, 5-Hydroxy isatoic anhydride serves as a crucial building block in the creation of agrochemicals, playing a significant role in the synthesis of compounds that can protect crops and enhance agricultural productivity.
Used in Organic Synthesis:
5-Hydroxy isatoic anhydride is utilized as a versatile reactant in organic synthesis, enabling the formation of diverse derivatives that are valuable for further chemical reactions and the development of new chemical entities.
Used in Medicinal Chemistry Research:
5-HYDROXY ISATOIC ANHYDRIDE is employed as a subject of study in medicinal chemistry for its potential antioxidant and antimicrobial properties, which could lead to the discovery of novel treatments and preventive measures in medicine.

InChI:InChI=1/C8H5NO4/c10-4-1-2-6-5(3-4)7(11)13-8(12)9-6/h1-3,10H,(H,9,12)

Upstream product

• 394-31-0 2-amino-5-hydroxybenzoic acid 
• 541-41-3 chloroformic acid ethyl ester 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 75-44-5 phosgene 
• 116-16-5 1,1,1,3,3,3-hexachloro-propan-2-one 
• 567-62-4 2-amino-5-hydroxybenzoic acid 

Downstream Products

• 909391-39-5 2-amino-5-hydroxy-N-(isopropylcarbamoylmethyl)benzamide 
• 931399-16-5 ethyl 4-hydroxy-2-oxo-1-(phenylmethyl)-6-[(phenylmethyl)oxy]-1,2-dihydro-3-quinolinecarboxylate 
• 85654-22-4 2-hydroxy-7,8-dihydro-6H,11H-pyrrolo[2,1-b]quinazolin-11-one 
• 1393714-23-2 13-methyl-6,8,13,13a-tetrahydro-5H-isoquinolino[1,2-b]quinazolin-10-yl(3-methoxyphenyl) carbamate 
• 1393714-24-3 13-methyl-6,8,13,13a-tetrahydro-5H-isoquinolino[1,2-b]quinazolin-10-yl o-tolylcarbamate 
• 1393714-25-4 13-methyl-6,8,13,13a-tetrahydro-5H-isoquinolino[1,2-b]quinazolin-10-yl(4-isopropylphenyl) carbamate 
• 929859-22-3 7-(benzyloxy)-2,3-dihydropyrrolo[2,1-b]quinazolin-9(1H)-one 
• 1393714-38-9 7-(benzyloxy)-4-methyl-9-oxo-1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolin-4-ium iodide 
• 1393714-39-0 7-(benzyloxy)-1,2,3,3a,4,9-hexahydro-4-methylpyrrolo[2,1-b]quinazoline 
• 1393714-29-8 4-methyl-1,2,3,3a,4,9-hexahydropyrrolo[2,1-b]quinazolin-7-yl (3-methoxyphenyl)carbamate 
• 1393714-30-1 4-methyl-1,2,3,3a,4,9-hexahydropyrrolo[2,1-b]quinazolin-7-yl o-tolylcarbamate 
• 1393714-31-2 4-methyl-1,2,3,3a,4,9-hexahydropyrrolo[2,1-b]quinazolin-7-yl (4-isopropylphenyl)carbamate 
• 1539278-94-8 10-(benzyloxy)-13-methyl-13,13a-dihydro-5H-isoquinolino[1,2-b]quinazolin-8(6H)-one 
• 1608152-83-5 3-((3,4-dihydroisoquinolin-2(1H)-yl)methyl)-4-(methylamino)phenol 

Relevant articles and documents

Discovery of Highly Selective and Nanomolar Carbamate-Based Butyrylcholinesterase Inhibitors by Rational Investigation into Their Inhibition Mode

Butyrylcholinesterase (BChE) is a promising target for the treatment of later stage cognitive decline in Alzheimer's disease. A set of pseudo-irreversible BChE inhibitors with high selectivity over hAChE was synthesized based on carbamates attached to tetrahydroquinazoline scaffolds with the 2-thiophenyl compound 2p as the most potent inhibitor of eqBChE (KC = 14.3 nM) and also of hBChE (KC = 19.7 nM). The inhibitors transfer the carbamate moiety onto the active site under release of the phenolic tetrahydroquinazoline scaffolds that themselves act as neuroprotectants. By combination of kinetic data with molecular docking studies, a plausible binding model was probed describing how the tetrahydroquinazoline scaffold guides the carbamate into a close position to the active site. The model explains the influence of the carrier scaffold onto the affinity of an inhibitor just before carbamate transfer. This strategy can be used to utilize the binding mode of other carbamate-based inhibitors.

SUBSTITUTED BENZOTRIAZINONE METABOLITES OF A GPR139 AGONIST

Compounds that are mammalian metabolites of an agonist of G-protein-coupled receptor 1.39 (GPR139), intermediates used in the synthesis of such metabolites, pharmaceutical compositions comprising such metabolites, and the use of such metabolites as biomar

Highly Selective Butyrylcholinesterase Inhibitors with Tunable Duration of Action by Chemical Modification of Transferable Carbamate Units Exhibit Pronounced Neuroprotective Effect in an Alzheimer's Disease Mouse Model

In this study, the carbamate structure of pseudo-irreversible butyrylcholinesterase (BChE) inhibitors was optimized with regard to a longer binding to the enzyme. A set of compounds bearing different heterocycles (e.g., morpholine, tetrahydroisoquinoline, benzimidazole, piperidine) and alkylene spacers (2 to 10 methylene groups between carbamate and heterocycle) in the carbamate residue was synthesized and characterized in vitro for their binding affinity, binding kinetics, and carbamate hydrolysis. These novel BChE inhibitors are highly selective for hBChE over human acetycholinesterase (hAChE), yielding short-, medium-, and long-acting nanomolar hBChE inhibitors (with a half-life of the carbamoylated enzyme ranging from 1 to 28 h). The inhibitors show neuroprotective properties in a murine hippocampal cell line and a pharmacological mouse model of Alzheimer's disease (AD), suggesting a significant benefit of BChE inhibition for a disease-modifying treatment of AD.

Quinolines from the cyclocondensation of isatoic anhydride with ethyl acetoacetate: Preparation of ethyl 4-hydroxy-2-methylquinoline-3-carboxylate and derivatives

A convenient two-step synthesis of ethyl 4-hydroxy-2-methylquinoline-3-carboxylate derivatives has been developed starting from commercially available 2-aminobenzoic acids. In step 1, the anthranilic acids are smoothly converted to isatoic anhydrides using solid triphosgene in THF. In step 2, the anhydride electrophiles are reacted with the sodium enolate of ethyl acetoacetate, generated from sodium hydroxide, in warm N,N-dimethylacetamide resulting in the formation of substituted quinolines. A degradation–buildup strategy of the ethyl ester at the 3-position allowed for the construction of the α-hydroxyacetic acid residue required for the synthesis of key arylquinolines involved in an HIV integrase project.

METHOD OF PRODUCING NITROGEN-CONTAINING HETEROCYCLIC COMPOUND

PROBLEM TO BE SOLVED: To provide a chemical compound production method realizing easy and high-yield production of a nitrogen-containing heterocyclic compound useful as a synthetic intermediate and the like in many fields such as medicine, agriculture and synthetic resin additives. SOLUTION: In the production method, an ortho-substituted benzene azide derivative represented by formula (1) is reacted with carbon dioxide in the presence of a reductant to obtain a compound represented by formula (2). [R is H and/or a substituent; A is an intramolecular cyclizable group; and B is a divalent linking group of C, N and O. COPYRIGHT: (C)2016,JPOandINPIT

Investigation into selective debenzylation and ring cleavage of quinazoline based heterocycles

The selective cleavage of different benzyl bonds within tetrahydroquinazoline and dihydroquinazolinone derived structures can be achieved by the usage of different reduction and debenzylation conditions thereby providing selective removal of O-benzyl protection groups as well as the cleavage of the ring structure within the quinazoline and quinazolinone systems.

INHIBITORS OF DNA GYRASE FOR THE TREATMENT OF BACTERIAL INFECTIONS

The present invention relates to compounds which specifically inhibit bacterial DNA Gyrase and can be used for the treatment of respiratory tract infections.

A simple heterocyclic fusion reaction and its application for expeditious syntheses of rutaecarpine and its analogs

In the search for new inhibitors of cholinesterases, a simple heterocyclic fusion reaction of isatoic anhydride 8 and 3,4-dihydroisoquinoline 22 was discovered which involves a spontaneous dehydrogenation upon heating. Applying the reaction, the bioactive natural alkaloid rutaecarpine and several substituted derivatives out of tryptamines and anthranilic acids or isatoic anhydrides, respectively, can be synthesized without tedious chromatographic purification. This provides simple and fast access to larger amounts of compounds with this privileged structure in medicinal chemistry.

Neuroprotective tri- and tetracyclic BChE inhibitors releasing reversible inhibitors upon carbamate transfer

Tri- and tetracyclic nitrogen-bridgehead compounds were designed and synthesized to yield micromolar cholinesterase (ChE) inhibitors. Structure-activity relationships identified potent compounds with butyrylcholinesterase selectivity. These compounds were selected as starting points for the design and synthesis of carbamate-based (pseudo)irreversible inhibitors. Compounds with superior inhibitory activity and selectivity were obtained and kinetically characterized also with regard to the velocity of enzyme carbamoylation. Structural elements were identified and introduced that additionally showed neuroprotective properties on a hippocampal neuronal cell line (HT-22) after glutamate-induced intracellular reactive oxygen species generation. We have identified potent and selective pseudoirreversible butyrylcholinesterase inhibitors that release reversible inhibitors with neuroprotective properties after carbamate transfer to the active site of cholinesterases.

Synthesis and SAR studies of novel 2-(4-oxo-2-aryl-quinazolin-3(4H)-yl) acetamide vasopressin V1b receptor antagonists

Synthesis and structure-activity relationships (SAR) of a novel series of vasopressin V1b (V3) antagonists are described. 2-(4-Oxo-2-aryl-quinazolin-3(4H)-yl)acetamides have been identified with low nanomolar affinity for the V1