7-[(3-Chloro-6,11-dihydro-6-methyl-5,5-dioxidodibenzo[c,f][1,2]thiazepin-11-yl)amino]heptanoic acid ethyl ester
[CAS# 66981-77-9]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: 7-[(3-Chloro-6,11-dihydro-6-methyl-5,5-dioxidodibenzo[c,f][1,2]thiazepin-11-yl)amino]heptanoic acid ethyl ester
• Synonyms: 7-[(3-Chloro-6,11-dihydro-6-methyldibenzo[c,f][1,2]thiazepin-11-yl)amino]heptanoic acid ethyl ester S,S-dioxide
• Molecular Formula: C₂₃H₂₉ClN₂O₄S
• Molecular Weight: 465.01
• CAS Registry Number: 66981-77-9
• SMILES: CCOC(=O)CCCCCCNC1C2=C(C=C(C=C2)Cl)S(=O)(=O)N(C3=CC=CC=C13)C

Properties

• Solubility: Insoluble (5.1E^-4 g/L) (25 °C), Calc.^*
• Density: 1.30±0.1 g/cm³ (20 °C 760 Torr), Calc.^*
• Boiling point: 573.3±60.0 °C 760 mmHg (Calc.)^*
• Flash point: 300.5±32.9 °C (Calc.)^*
• Index of refraction: 1.606 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Discovery and Applications

7-[(3-Chloro-6,11-dihydro-6-methyl-5,5-dioxidodibenzo[c,f][1,2]thiazepin-11-yl)amino]heptanoic acid ethyl ester is a chemical compound structurally characterized by a dibenzo-thiazepine core with specific substitutions that confer unique pharmacological properties. The compound features a thiazepine ring system fused to two benzene rings, with chlorine substitution at the 3-position and methylation at the 6-position. Additionally, the compound contains two sulfone groups (5,5-dioxidation) that impact its electronic and steric profile. Attached to the thiazepine moiety at position 11 is an amino substituent linked to a heptanoic acid ethyl ester side chain, which influences the compound’s solubility and bioavailability.

This compound has been studied primarily for its potential medicinal applications, especially in targeting neurological or inflammatory pathways due to the presence of the thiazepine scaffold, a known motif in various pharmacologically active agents. The sulfone functionalities enhance the metabolic stability and polarity, which can improve drug-like properties. The ethyl ester side chain serves as a prodrug moiety, often used to improve membrane permeability and facilitate absorption before enzymatic cleavage releases the active acid form.

In terms of synthesis, this compound is typically obtained through multi-step organic synthesis involving the construction of the dibenzo-thiazepine core, selective chlorination, oxidation to introduce the sulfone groups, and subsequent amination and esterification to append the heptanoic acid ethyl ester side chain. The synthetic route must be carefully controlled to maintain regio- and stereochemical integrity, especially because the biological activity is sensitive to structural variations.

The compound’s applications remain largely experimental, with ongoing research focusing on its potential as an anti-inflammatory, neuroprotective, or analgesic agent. Preclinical studies often explore its binding affinities to various receptor subtypes and enzymes involved in inflammatory cascades or neurotransmitter modulation. The compound’s pharmacokinetic profile, including absorption, distribution, metabolism, and excretion, is a key focus to optimize dosing regimens and minimize side effects.

Due to the complex structure and the presence of multiple functional groups, the compound also serves as a useful chemical scaffold for medicinal chemists to develop derivatives with enhanced potency or selectivity. Modifications on the thiazepine ring, the sulfone groups, or the ester side chain allow exploration of structure-activity relationships (SAR) that guide drug development.

References

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