223671-80-5

Basic information

• Product Name: 1,4-Dichloro-7-isoquinolinesulfonyl Chloride
• Synonyms: 1,4-Dichloro-7-isoquinolinesulfonyl Chloride;1,4-dichloro-7-isoquinolinesulphonyl chloride;7-ISOQUINOLINESULFONYL CHLORIDE, 1,4-DICHLORO-
• CAS NO: 223671-80-5
• Molecular Formula: C₉H₄Cl₃NO₂S
• Molecular Weight: 296.56
• Product Categories: All Inhibitors;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;Inhibitors, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 223671-80-5.mol
• Article Data: 5

Chemical Properties

• Melting Point: 97-99°C
• Appearance: /
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform, DMSO
• CAS DataBase Reference: 1,4-Dichloro-7-isoquinolinesulfonyl Chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-Dichloro-7-isoquinolinesulfonyl Chloride(223671-80-5)
• EPA Substance Registry System: 1,4-Dichloro-7-isoquinolinesulfonyl Chloride(223671-80-5)

Safety Data

• Hazardous Substances Data: 223671-80-5(Hazardous Substances Data)

Usage

Description

1,4-Dichloro-7-isoquinolinesulfonyl Chloride is an off-white solid that serves as an intermediate in the synthesis of isoquinolinylguanidines, which are known to act as urokinase inhibitors. This chemical compound plays a crucial role in the development of pharmaceuticals targeting specific enzyme inhibition for therapeutic purposes.

Uses

Used in Pharmaceutical Industry:
1,4-Dichloro-7-isoquinolinesulfonyl Chloride is used as an intermediate for the synthesis of isoquinolinylguanidines, which are urokinase inhibitors. The application reason is to develop pharmaceuticals that can inhibit urokinase, an enzyme involved in various physiological processes, including tissue remodeling and cancer progression. By inhibiting urokinase, these compounds can potentially be used in the treatment of conditions where this enzyme plays a detrimental role, such as certain types of cancer.

Upstream product

• 223671-81-6 4-chloro-1-oxo-1,2-dihydro-7-isoquinolinesulfonyl chloride 
• 60-29-7 diethyl ether 
• 491-30-5 1-isoquinolone 
• 56241-09-9 4-chloro-1-(2H)-isoquinolone 
• 223671-13-4 7-bromo-1,4-dichloroisoquinoline 

Downstream Products

• 256477-48-2 N-benzyl-N-[(1,4-dichloro-7-isoquinolinyl)sulphonyl]-L-alanine tert-butyl ester 
• 256477-68-6 methyl 1-{[(1,4-dichloro-7-isoquinolinyl)sulphonyl]amino}cyclohexanecarboxylate 
• 256477-24-4 tert-butyl 2-{[(1,4-dichloro-7-isoquinolinyl)sulphonyl]amino}benzoate 
• 256477-25-5 tert-butyl 3-{[(1,4-dichloro-7-isoquinolinyl)sulphonyl]amino}benzoate 
• 256477-30-2 N-[(1,4-dichloro-7-isoquinolinyl)sulphonyl]-N-phenylglycine tert-butyl ester 
• 256477-34-6 N-[(1,4-dichloro-7-isoquinolinyl)sulphonyl]-N-benzylglycine t-butyl ester 
• 256477-26-6 Methyl 3-{[(1,4-dichloro-7-isoquinolinyl)sulphonyl]amino}-4-methoxybenzoate 
• 256478-25-8 N-[(4-chloro-1-guanidino-7-isoquinolinyl)sulphonyl]-N-benzylglycine tert-butyl ester 
• 256478-17-8 tert-butyl 3-{[(4-chloro-1-guanidino-7-isoquinolinyl)sulphonyl]amino}benzoate 
• 256478-16-7 tert-butyl 2-{[(4-chloro-1-guanidino-7-isoquinolinyl)sulphonyl]amino}benzoate 
• 256478-54-3 methyl 1-{[(4-chloro-1-guanidino-7-isoquinolinyl)sulphonyl]amino}cyclohexanecarboxylate 
• 256478-37-2 N-benzy-N-[(4-chloro-1-guanidino-7-isoquinolinyl)sulphonyl]-L-alanine tert-butyl ester 
• 256477-54-0 N-[(1,4-dichloro-7-isoquinolinyl)sulphonyl]-L-phenylalanine t-butyl ester 
• 256478-22-5 N-[(4-chloro-1-guanidino-7-isoquinolinyl)sulphonyl]-N-phenylglycine 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.

ISOQUINOLINES AS UROKINASE INHIBITORS

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Isoquinolines

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