182182-31-6 | N-(8-Amino-6-fluoro-5-methyl-1-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)acetamide

CAS:182182-31-6 | N-(8-Amino-6-fluoro-5-methyl-1-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)acetamide,Description

“N-(8-Amino-6-fluoro-5-methyl-1-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)acetamide” is a chemical compound with the molecular formula C13H15FN2O2. It is an important pharmaceutical raw material and is a by-product of the ezetimibe preparation process.

Molecular Structure Analysis

The molecular structure of this compound can be represented by the InChI code: 1S/C13H15FN2O2/c1-6-8-3-4-11(16-7(2)17)13(18)12(8)10(15)5-9(6)14/h5,11H,3-4,15H2,1-2H3,(H,16,17). The Canonical SMILES representation is: CC1=C(C=C(C2=C1CCC(C2=O)NC(=O)C)N)F.

Physical And Chemical Properties Analysis

This compound has a molecular weight of 250.27 g/mol. It has a hydrogen bond donor count of 2 and a hydrogen bond acceptor count of 4. The exact mass is 250.11175589 g/mol. The compound is solid at room temperature.

Scientific Research Applications

Synthesis Methods and Chemical Structures

• A study outlined a regioselective oxidation process for synthesizing amino ketones from N-indan-4-yl-acetamide or N-(5,6,7,8-tetrahydronaphthalen-1-yl)acetamide, which were then converted to corresponding halogenated derivatives, showcasing a method for creating halogen-substituted naphthalenes (Nguyen et al., 2003).
• Another study involved the synthesis and resolution of melatonin receptor agents, including derivatives of tetrahydronaphthalenic, highlighting the importance of chiral separations in drug discovery (Lipka-Belloli et al., 2001).

Anticancer Agents and Pharmacology

• Research on 1,3,4-oxadiazole derivatives investigated their cytotoxic effects on various cancer cell lines, revealing the potential of tetrahydronaphthalen-based compounds as anticancer agents. These compounds showed significant effects on apoptosis and caspase-3 activation, along with inhibitory activities on Akt and FAK signaling pathways (Altıntop et al., 2018) .

Molecular Interactions and Analysis

• A study on the competition between hydrogen, stacking, and halogen bonding in a related compound provided insights into the molecular interactions stabilizing crystal packing. This research highlights the complexity of noncovalent interactions in molecular structures and their significance in drug design (Gouda et al., 2022).

Herbicidal Activity

• The synthesis and evaluation of herbicidal activity in certain derivatives demonstrated the versatility of naphthalene-based compounds beyond pharmacological applications, indicating their potential in agricultural chemistry (Huang & Zhong-cheng, 2006).

Safety And Hazards

The compound has a GHS07 pictogram, with the signal word “Warning”. The hazard statements include H302, H315, H319, H335, and the precautionary statement is P261. More detailed safety information can be found in the MSDS.

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