132997-77-4

Basic information

• Product Name: 1-CHLORO-6-METHOXY-ISOQUINOLINE
• Synonyms: 1-CHLORO-6-METHOXY-ISOQUINOLINE;Isoquinoline, 1-chloro-6-Methoxy-;6-Methoxy-1-chloroisoquinoline
• CAS NO: 132997-77-4
• Molecular Formula: C₁₀H₈ClNO
• Molecular Weight: 193.63
• Product Categories: Heterocycles
• Mol File: 132997-77-4.mol

Chemical Properties

• Melting Point: 77℃
• Boiling Point: 332.992 °C at 760 mmHg
• Flash Point: 155.188 °C
• Appearance: /
• Density: 1.268 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.622
• Storage Temp.: 2-8°C
• PKA: 2.75±0.38(Predicted)
• CAS DataBase Reference: 1-CHLORO-6-METHOXY-ISOQUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-CHLORO-6-METHOXY-ISOQUINOLINE(132997-77-4)
• EPA Substance Registry System: 1-CHLORO-6-METHOXY-ISOQUINOLINE(132997-77-4)

Safety Data

• Hazardous Substances Data: 132997-77-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-Chloro-6-Methoxy-Isoquinoline is used as a potential anti-inflammatory agent for its capacity to reduce inflammation, a common pathological process in various diseases.
1-Chloro-6-Methoxy-Isoquinoline is used as a potential analgesic agent for its ability to alleviate pain, offering a potential alternative for pain management.
Used in Antifungal Applications:
1-Chloro-6-Methoxy-Isoquinoline is used as an antifungal agent, exhibiting activity against various fungal species, which could be beneficial in treating fungal infections.
Used in Anticancer Applications:
1-Chloro-6-Methoxy-Isoquinoline is used as a potential anticancer agent, showing promise in inhibiting the growth and proliferation of cancer cells, and potentially offering a new avenue for cancer treatment.
Used in Medicinal Chemistry Research:
1-Chloro-6-Methoxy-Isoquinoline is used as a subject of research for its unique structure and properties, contributing to the advancement of knowledge in medicinal chemistry and the development of new drugs.

InChI:InChI=1/C10H8ClNO/c1-13-8-2-3-9-7(6-8)4-5-12-10(9)11/h2-6H,1H3

Upstream product

• 26829-43-6 6-methoxy-2H-isoquinolin-1-one 
• 266690-46-4 6-methoxy-isoquinoline-N-oxide hydrochloride 
• 26829-43-6 6-methoxy-2H-isoquinolin-1-one 
• 6099-04-3 3-methoxycinnamic acid 
• 6099-04-3 trans-3-methoxycinnamic acid 
• 139583-91-8 2-methyl-4-methoxybenzamide 
• 6245-57-4 4-methoxy-2-methylbenzoic acid 
• 31310-08-4 2-methyl-4-methoxybenzoyl chloride 
• 900174-96-1 (E)-4-methoxy-2-methylbenzoyl-(N,N-dimethyl)formamidine 
• 52986-70-6 6-methoxyisoquinoline 

Downstream Products

• 266690-47-5 6-methoxy-1-phenoxy-isoquinoline 
• 26829-43-6 6-methoxy-2H-isoquinolin-1-one 
• 1613479-60-9 C₁₆H₁₁F₂NO₂ 
• 850197-67-0 1-chloroisoquinolin-6-ol 
• 266690-48-6 1-amino-6-methoxy-isoquinoline 

Relevant articles and documents

Discovery of a 4-aryloxy-1H-pyrrolo[3,2-c]pyridine and a 1-aryloxyisoquinoline series of TRPA1 antagonists

A series of TRPA1 antagonists is described having a 4-aryloxy-1H-pyrrolo[3,2-c]pyridine or a 1-aryloxyisoquinoline scaffold. These compounds have high ligand efficiency and favorable physical properties and may thus serve as scaffolds for further optimization.

Discovery and early clinical evaluation of BMS-605339, a potent and orally efficacious tripeptidic acylsulfonamide ns3 protease inhibitor for the treatment of hepatitis C virus infection

The discovery of BMS-605339 (35), a tripeptidic inhibitor of the NS3/4A enzyme, is described. This compound incorporates a cyclopropylacylsulfonamide moiety that was designed to improve the potency of carboxylic acid prototypes through the introduction of favorable nonbonding interactions within the S1′ site of the protease. The identification of 35 was enabled through the optimization and balance of critical properties including potency and pharmacokinetics (PK). This was achieved through modulation of the P2* subsite of the inhibitor which identified the isoquinoline ring system as a key template for improving PK properties with further optimization achieved through functionalization. A methoxy moiety at the C6 position of this isoquinoline ring system proved to be optimal with respect to potency and PK, thus providing the clinical compound 35 which demonstrated antiviral activity in HCV-infected patients.

Compounds for PIM kinase inhibition and for treating malignancy

The present invention relates to the compounds of formula I as well as to their use as PIM kinase inhibitors and, thereby, their use for treating oncological diseases, particularly of the hematopoietic system, the liver and the prostate gland

Fragment-based discovery of 6-substituted isoquinolin-1-amine based ROCK-I inhibitors

Fragment-based NMR screening of a small literature focused library led to identification of a historical thrombin/FactorXa building block, 17A, that was found to be a ROCK-I inhibitor. In the absence of an X-ray structure, fragment growth afforded 6-substituted isoquinolin-1-amine derivatives which were profiled in the primary ROCK-I IMAP assay. Compounds 23A and 23E were selected as fragment optimized hits for further profiling. Compound 23A has similar ROCK-1 affinity, potency and cell based efficacy to the first generation ROCK inhibitors, however, it has a superior PK profile in C57 mouse. Compound 23E demonstrates the feasibility of improving ROCK-1 affinity, potency and cell based efficacy for the series, however, it has a poor PK profile relative to 23A.

COMPOUNDS FOR PIM KINASE INHIBITION AND FOR TREATING MALIGNANCY

The present invention relates to the compounds of formula (I) as well as to their use as PIM kinase inhibitors and, thereby, their use for treating oncological diseases, particularly of the hematopoietic system, the liver and the prostate gland.

Hepatitis C Virus Inhibitors

Hepatitis C virus inhibitors having the general formula are disclosed. Compositions comprising the compounds and methods for using the compounds to inhibit HCV are also disclosed.

INHIBITORS OF CATHEPSIN B

The present invention is directed to a method of using compounds of Formula (I) to inhibit Cathepsin B. Specifically the compounds of the present invention are useful as therapeutic agents for the treatment of tumor invasion, metastasis, Alzheimer's Disease, arthritis, inflammatory diseases such as chronic and acute pancreatitis, inflammatory airway disease, and bone and joint disorders, including osteoporosis, osteoarthritis, rheumatoid arthritis, psoriasis, and other autoimmune disorders, liver fibrosis, including liver fibrosis associated with HCV, all types of steatosis (including non-alcoholic steatohepatitis) and alcohol-associated steatohepatitis, non-alcoholic fatty liver disease, forms of pulmonary fibrosis including idiopathic pulmonary fibrosis, pathological diagnosis of interstitial pneumonia following lung biopsy, renal fibrosis, cardiac fibrosis, retinal angiogenesis and fibrosis/gliosis in the eye, schleroderma, and systemic sclerosis. The compounds of Formula (I) are also useful for treating subjects with both HCV and fibrosis in a mammal, particularly liver fibrosis, and subjects affirmatively diagnosed or at risk for both HCV and liver fibrosis.

6-SUBSTITUTED ISOQUINOLINE DERIVATIVES

The present invention relates to 6-substituted isoquinoline derivatives having the general Formula I wherein X is O, S or NH; Y is OH or NH2; m is 0, 1 or 2; n is 0 or 1; o is 0 or 1; R1 is H, when Y is NH2; or R1 is H, (C1-4)alkyl or halogen, when Y is OH; R2 and R3 are independently H, (C1-4)alkyl or halogen; R4 is H or (C1-6)alkyl, optionally substituted with halogen, (C3-7)cycloalkyl, (C6-10)aryl or a saturated 5- or 6-membered heterocyclic ring comprising 1-3 heteroatoms independently selected from O, S and N, the (C6-10)aryl and heterocyclic ring being optionally substituted with (C1-4)alkyl, (C1-4)alkyloxy or halogen; R5 is H or (C1-4)alkyl; or a pharmaceutically acceptable salt thereof, with the proviso that the compounds of Formula I wherein X is O, Y is OH , n is 0 and m+o=2 are excluded, to pharmaceutical compositions comprising the same, as well as to the use of said 6-substituted isoquinoline derivatives for the preparation of a medicament for the treatment of ROCK-I related disorders such as glaucoma, hypertension and atherosclerosis.

Hepatitis C Virus Inhibitors

Hepatitis C virus inhibitors having the general formula are disclosed. Compositions comprising the compounds and methods for using the compounds to inhibit HCV are also disclosed.

HCV INHIBITORS

The present invention is directed to compounds that are antiviral agents. Specifically the compounds of the present invention inhibit replication of HCV and are therefore useful in treating hepatitis C infections. The present invention is also directed to pharmaceutical compositions comprising these compounds and processes for preparing them.