187963-07-1

Basic information

• Product Name: 1-CHLORO-5-METHOXY-3,4-DIHYDRO-NAPHTHALENE-2-CARBALDEHYDE
• Synonyms: 1-CHLORO-5-METHOXY-3,4-DIHYDRO-NAPHTHALENE-2-CARBALDEHYDE
• CAS NO: 187963-07-1
• Molecular Formula: C₁₂H₁₁ClO₂
• Molecular Weight: 222.67
• Mol File: 187963-07-1.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-CHLORO-5-METHOXY-3,4-DIHYDRO-NAPHTHALENE-2-CARBALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-CHLORO-5-METHOXY-3,4-DIHYDRO-NAPHTHALENE-2-CARBALDEHYDE(187963-07-1)
• EPA Substance Registry System: 1-CHLORO-5-METHOXY-3,4-DIHYDRO-NAPHTHALENE-2-CARBALDEHYDE(187963-07-1)

Safety Data

• Hazardous Substances Data: 187963-07-1(Hazardous Substances Data)

Usage

General Description

1-Chloro-5-methoxy-3,4-dihydro-naphthalene-2-carbaldehyde is a chemical compound with the molecular formula C12H11ClO2. It is an aldehyde derivative of naphthalene, containing a chlorine atom and a methoxy group. This chemical is commonly used in organic synthesis and pharmaceutical research as an intermediate in the preparation of various compounds. It has potential applications in the development of drugs and agrochemicals due to its structural properties and reactivity. The compound may also be used in the production of perfumes and flavoring agents. However, it is important to handle this chemical with care, as it may pose health and environmental hazards.

Upstream product

• 33892-75-0 5-Methoxy-1-tetralone 
• 68-12-2 N,N-dimethyl-formamide 

Relevant articles and documents

Synthesis of a series of diaminobenzo[f]- and diaminobenzo[h]pyrimido[4,5-b]quinolines as 5-daza tetracyclic nonclassical antifolates

A series of diaminobenzo[f]- and diaminobenzo[h]pyrimido[4,5-b]quinolines 1-11 were designed as 5-deaza tetracyclic nonclassical, lipophilic antifolates. The compounds were designed as conformationally semi-rigid and rigid analogs of 2,4-diamino-6-phenyl- 12 and 2,4-diamino-7-phenylpyrido[2,3-d]pyrimidines 13 and 14. The target compounds were synthesized by cyclocondensation of chlorovinyl aldehydes obtained from appropriately substituted 1- or 2-tetralone, with 2,4,6-triaminopyrimidine. Compounds 1-11 were evaluated as inhibitors of P. carinii and T. gondii dihydrofolate reductases. These pathogens cause fatal opportunistic infections in AIDS patients. In addition, the selectivity of these agents was evaluated using rat liver dihydrofolate reductase as the mammalian source. In general the benzo[f]pyrimido[4,5-b]quinolines 1-5 were more potent than the corresponding benzo[h]pyrimido[4,5-b]quinoline analogues 6-11 against P. carinii and rat liver dihydrofolate reductase and were equipotent against T. gondii dihydrofolate reductase. Compounds 6-11 were moderately selective towards T. gondii dihydrofolate reductase with IC50s in the 10-7 M range. In contrast analogues 1-5 lacked selectivity against P. carinii or T. gondii dihydrofolate reductase and were, in general, potent inhibitors of rat liver dihydrofolate reductase with IC50s in the 10-8 M range. Analogues 1 and 4 were evaluated against a series of tumor cell lines in vitro and were found to have moderate antitumor activity (IC50 10-6 M). The structure activity/selectivity relationships suggest that benzo[f]pyrimido analogues 1-5 with the phenyl ring substitution in the 'upper' portion of the tetracyclic ring are better accommodated within the rat liver (mammalian) dihydrofolate reductase and P. carinii dihydrofolate reductase active sites compared to the benzo[h]pyrimido analogues 6-11 which have the phenyl ring substitution in the 'lower' portion of the tetracyclic ring. In contrast P. gondii dihydrofolate reductase does not discriminate between the isomers and binds to both series of compounds with similar affinities.