223671-81-6

Basic information

• Product Name: 4-Chloro-1,2-dihydro-1-oxo-7-isoquinolinesulfonyl Chloride
• Synonyms: 4-Chloro-1,2-dihydro-1-oxo-7-isoquinolinesulfonyl Chloride;4-Chloro-1-hydroxy-7-isoquinolinesulfonyl Chloride
• CAS NO: 223671-81-6
• Molecular Formula: C₉H₅Cl₂NO₃S
• Molecular Weight: 278.11
• Product Categories: Heterocycles;Sulfonyl Chlorides;Heterocycles, Sulfonyl Chlorides
• Mol File: 223671-81-6.mol

Chemical Properties

• Melting Point: >250°C (dec.)
• Boiling Point: 519.4°C at 760 mmHg
• Flash Point: 267.9°C
• Appearance: /
• Density: 1.73g/cm³
• Vapor Pressure: 6.87E-11mmHg at 25°C
• Refractive Index: 1.677
• Storage Temp.: Refrigerator, Under Inert Atmosphere
• Solubility: DMSO, Methanol
• CAS DataBase Reference: 4-Chloro-1,2-dihydro-1-oxo-7-isoquinolinesulfonyl Chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chloro-1,2-dihydro-1-oxo-7-isoquinolinesulfonyl Chloride(223671-81-6)
• EPA Substance Registry System: 4-Chloro-1,2-dihydro-1-oxo-7-isoquinolinesulfonyl Chloride(223671-81-6)

Safety Data

• Hazardous Substances Data: 223671-81-6(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
4-Chloro-1,2-dihydro-1-oxo-7-isoquinolinesulfonyl Chloride is used as a synthetic building block for the creation of various organic compounds. Its unique chemical structure allows it to participate in a range of reactions, such as nucleophilic substitutions, electrophilic aromatic substitutions, and condensation reactions. This versatility makes it a valuable tool for the synthesis of complex organic molecules, including pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-Chloro-1,2-dihydro-1-oxo-7-isoquinolinesulfonyl Chloride is used as a key intermediate in the synthesis of various drug candidates. Its reactivity and structural diversity enable the development of novel therapeutic agents with improved pharmacological properties, such as enhanced potency, selectivity, and bioavailability. The compound's utility in organic synthesis allows for the exploration of new chemical space and the discovery of innovative drug candidates with potential applications in the treatment of various diseases and medical conditions.
Used in Agrochemical Industry:
4-Chloro-1,2-dihydro-1-oxo-7-isoquinolinesulfonyl Chloride also finds application in the agrochemical industry, where it is used as a starting material for the synthesis of various agrochemicals, such as pesticides and herbicides. Its unique chemical properties and reactivity enable the development of novel active ingredients with improved efficacy, selectivity, and environmental compatibility. This contributes to the ongoing efforts to develop more sustainable and effective solutions for crop protection and pest management.
Used in Research and Development:
In addition to its applications in the pharmaceutical and agrochemical industries, 4-Chloro-1,2-dihydro-1-oxo-7-isoquinolinesulfonyl Chloride is also used in research and development settings. Its unique chemical structure and reactivity make it an attractive candidate for the exploration of new reaction pathways and the development of innovative synthetic methodologies. This contributes to the advancement of chemical knowledge and the discovery of new synthetic strategies for the preparation of complex organic molecules.

InChI:InChI=1/C9H5Cl2NO3S/c10-8-4-12-9(13)7-3-5(16(11,14)15)1-2-6(7)8/h1-4H,(H,12,13)

Upstream product

• 491-30-5 1-isoquinolone 
• 56241-09-9 4-chloro-1-(2H)-isoquinolone 

Downstream Products

• 223671-80-5 1,4-dichloro-7-isoquinolinesulphonyl chloride 
• 256477-38-0 N-[(1,4-dichloro-7-isoquinolinyl)sulphonyl]-N-(2-methoxybenzyl)glycine t-butyl ester 
• 256477-32-4 N-[(1,4-Dichloro-7-isoquinolinyl)sulphonyl]-N-(cyclohexylmethyl)-glycine t-butyl ester 
• 256477-41-5 N-[(1,4-dichloro-7-isoquinolinyl)sulphonyl]-N-(3-chlorobenzyl)glycine t-butyl ester 
• 256477-42-6 N-[(1,4-dichloro-7-isoquinolinyl)sulphonyl]-N-(4-methoxybenzyl)glycine t-butyl ester 
• 256477-40-4 N-[(1,4-dichloro-7-isoquinolinyl)sulphonyl]-N-(3-methoxybenzyl)glycine t-butyl ester 
• 256478-24-7 N-[(4-chloro-1-guanidino-7-isoquinolinyl)sulphonyl]-N-(cyclohexylmethyl)glycine t-butyl ester 
• 739353-87-8 N-[(4-chloro-1-guanidino-7-isoquinolinyl)sulphonyl]-N-(4-methoxybenzyl)glycine t-butyl ester 

Relevant articles and documents

Selective urokinase-type plasminogen activator inhibitors. 4. 1-(7-Sulfonamidoisoquinolinyl)guanidines

1-Isoquinolinylguanidines were previously disclosed as potent and selective inhibitors of urokinase-type plasminogen activator (uPA). Further investigation of this template has revealed that incorporation of a 7-sulfonamide group furnishes a new series of potent and highly selective uPA inhibitors. Potency and selectivity can be achieved with sulfonamides derived from a variety of amines and is further enhanced by the incorporation of sulfonamides derived from amino acids. The binding mode of these 1-isoquinolinylguanidines has been investigated by X-ray cocrystallization studies. uPA inhibitor 26 was selected for further evaluation based on its excellent enzyme potency (Ki 10 nM) and selectivity profile (4000-fold versus tPA and 2700-fold versus plasmin). In vitro, compound 26 is able to inhibit exogenous uPA in human chronic wound fluid (IC50 = 0.89 μM). In vivo, in a porcine acute excisional wound model, following topical delivery, compound 26 is able to penetrate into pig wounds and inhibit exogenous uPA activity with no adverse effect on wound healing parameters. On the basis of this profile, compound 26 (UK-371,804) was selected as a candidate for further preclinical evaluation for the treatment of chronic dermal ulcers.

Composition for the treatment of damaged tissue

A pharmaceutical for use in damaged tissue, such as wound, treatment (e.g. healing) is described. The pharmaceutical comprising a composition which comprises: (a) a growth factor; and (b) an inhibitor agent; and optionally (c) a pharmaceutically acceptable carrier, diluent or excipient; wherein the inhibitor agent can inhibit the action of at least one specific adverse protein (e.g. a specific protease) that is upregulated in a damaged tissue, such as a wound, environment.

Isoquinolines as urokinase inhibitors

Compounds of formula (I): and pharmaceutically acceptable salts thereof, wherein one of R1 and R2 is H and the other is N=C(NH2)2 or NHC(=NH)NH2, and the other substituents are as defined herein, are urokinase (uPA) inhibitors.

Isoquinolines

Isoquinolinylguanidine compounds of formula (I): STR1 wherein the substituents are as defined herein, and salts thereof, are disclosed as urokinase inhibitors.