1011412-52-4

Basic information

• Product Name: 2-(3-chloropropyl)-3-(3,4-dimethoxyphenyl)-1-oxo-1,2,3,4-tetrahydroisoquinoline-4-carboxylic acid
• Synonyms: 2-(3-chloropropyl)-3-(3,4-dimethoxyphenyl)-1-oxo-1,2,3,4-tetrahydroisoquinoline-4-carboxylic acid;2-(3-Chloropropyl)-3-(3,4-dimethoxyphenyl)-1-oxo-1,2,3,4-tetrahydroisoquinoline-4-carboxylic a
• CAS NO: 1011412-52-4
• Molecular Formula: C21H22ClNO5
• Molecular Weight: 403.85608
• Mol File: 1011412-52-4.mol
• Article Data: 1

Chemical Properties

• Melting Point: 184-186°
• Boiling Point: 585.2±50.0 °C(Predicted)
• Appearance: /
• Density: 1.287±0.06 g/cm3(Predicted)
• PKA: 3.51±0.40(Predicted)
• CAS DataBase Reference: 2-(3-chloropropyl)-3-(3,4-dimethoxyphenyl)-1-oxo-1,2,3,4-tetrahydroisoquinoline-4-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(3-chloropropyl)-3-(3,4-dimethoxyphenyl)-1-oxo-1,2,3,4-tetrahydroisoquinoline-4-carboxylic acid(1011412-52-4)
• EPA Substance Registry System: 2-(3-chloropropyl)-3-(3,4-dimethoxyphenyl)-1-oxo-1,2,3,4-tetrahydroisoquinoline-4-carboxylic acid(1011412-52-4)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 1011412-52-4(Hazardous Substances Data)

Usage

Molecular structure

Carbon chain with a chlorine-substituted propyl group and a 3,4-dimethoxyphenyl ring.

Functional groups

Tetrahydroisoquinoline structure, carboxylic acid, and ketone groups.

Complexity

The compound has a complex and specific name, indicating a potentially complex chemical structure.

Pharmaceutical potential

Likely to have pharmaceutical or medicinal properties due to the presence of functional groups commonly found in drug molecules.

Further research needed

Exact use and properties would need to be determined through additional research and analysis.

Upstream product

• 703-59-3 homophthalic anhydride 
• 120-14-9 3,4-dimethoxy-benzaldehyde 

Relevant articles and documents

Synthesis of new indeno[1,2-c]isoquinolines: Cytotoxic non-camptothecin topoisomerase I inhibitors

In an attempt to design and synthesize potential anticancer agents acting by inhibition of topoisomerase I (top1), a new series of indenoisoquinolines was prepared and tested for cytotoxicity in human cancer cell cultures and for activity against top1. The synthesis relied on the condensation of substituted Schiff bases with homophthalic anhydrides to produce cis-3-aryl-4-carboxyisoquinolones that were cyclized to indenoisoquinolines in the presence of thionyl chloride. Both top1 inhibitory activity and cytotoxicity maximized in a single compound, 6-[3-(2-hydroxyethyl)aminopropyl]-5,6-dihydro-2,3-dimethoxy-8,9-methylenediox y-5,11-dioxo-11H-indeno [1,2-c] isoquinoline hydrochloride (19a), which proved to be a very potent top1 inhibitor having a 110 nM mean graph midpoint (MGM) when tested for cytotoxicity in 55 human cancer cell cultures. A number of structurally related indenoisoquinolines were also obtained that had both potent cytotoxicity as well as top1 inhibitory activity. The key feature of the more potent compounds was the presence of an aminoalkyl side chain on the indenoisoquinoline nitrogen atom. The DNA cleavage patterns induced by top1 in the presence of the indenoisoquinolines were different from those seen with camptothecin. Some of the cleavage sites induced by the indenoisoquinolines were different from those seen with camptothecin, and conversely, camptothecin induced unique cleavage sites not apparent with the indenoisoquinolines. However, both camptothecin and the indenoisoquinolines also induced DNA cleavage sites that were the same in both series but varied in intensity. In addition, some of the DNA cleavages seen with the free base of 19a (compound 18c) in the presence of top1 were inhibited at higher drug concentrations, suggesting either a direct inhibition of the enzyme or an alternative mechanism involving DNA intercalation. Consistent with intercalation, compound 18c did unwind DNA.