Cas no 885340-11-4 (7-Descarboxamido, 7-Cyano (R)-Silodosin O-Benzoate)

7-Descarboxamido, 7-Cyano (R)-Silodosin O-Benzoate structure
885340-11-4 structure
Product Name:7-Descarboxamido, 7-Cyano (R)-Silodosin O-Benzoate
CAS No:885340-11-4
MF:C32H34F3N3O4
MW:581.625278949738
CID:1081016
Update Time:2025-11-01

7-Descarboxamido, 7-Cyano (R)-Silodosin O-Benzoate Chemical and Physical Properties

Names and Identifiers

    • 1-(3-benzoyloxypropyl)-7-cyano-5-(2R-{2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl}aminopropyl)-2,3-dihydroindole
    • 1-[3-(benzoyloxy)propyl]-2,3-dihydro-5-[(2R)-2-[[2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl]amino]propyl]-1H-Indole-7-carbonitrile
    • 7-Descarboxamido, 7-Cyano (R)-Silodosin O-Benzoate
    • 1-[3-(Benzoyloxy)propyl]-2,3-dihydro-5-[(2R)-2-[[2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl]amino]propyl]-1H-indole-7-carbonitrile (ACI)
    • 3-[7-Cyano-5-[(2R)-2-([2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl]amino)propyl]-2,3-dihydro-indol-1-yl]propyl benzoate
    • Inchi: 1S/C32H34F3N3O4/c1-23(37-13-17-40-28-10-5-6-11-29(28)42-22-32(33,34)35)18-24-19-26-12-15-38(30(26)27(20-24)21-36)14-7-16-41-31(39)25-8-3-2-4-9-25/h2-6,8-11,19-20,23,37H,7,12-18,22H2,1H3/t23-/m1/s1
    • InChI Key: HUKYYZXALLLJJL-HSZRJFAPSA-N
    • SMILES: C(N1CCC2=CC(=CC(=C12)C#N)C[C@@H](C)NCCOC1C=CC=CC=1OCC(F)(F)F)CCOC(C1C=CC=CC=1)=O

Experimental Properties

  • Density: 1.28

7-Descarboxamido, 7-Cyano (R)-Silodosin O-Benzoate Pricemore >>

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7-Descarboxamido, 7-Cyano (R)-Silodosin O-Benzoate Production Method

Production Method 1

Reaction Conditions
1.1 Reagents: Sodium carbonate Solvents: tert-Butanol ;  reflux
1.2 Solvents: Isopropanol
Reference
Improved Preparation of Silodosin
Liu, Hui ; Lv, Fei; Liu, Yuan, Organic Preparations and Procedures International, 2019, 51(3), 287-293

7-Descarboxamido, 7-Cyano (R)-Silodosin O-Benzoate Raw materials

7-Descarboxamido, 7-Cyano (R)-Silodosin O-Benzoate Preparation Products

7-Descarboxamido, 7-Cyano (R)-Silodosin O-Benzoate Related Literature

Additional information on 7-Descarboxamido, 7-Cyano (R)-Silodosin O-Benzoate

Professional Introduction to 7-Descarboxamido, 7-Cyano (R)-Silodosin O-Benzoate and CAS No. 885340-11-4

7-Descarboxamido, 7-Cyano (R)-Silodosin O-Benzoate is a sophisticated chemical compound that has garnered significant attention in the field of pharmaceutical research and development. This compound, identified by the CAS number 885340-11-4, represents a derivative of Silodosin, a well-known alpha-adrenergic receptor antagonist primarily used in the treatment of benign prostatic hyperplasia (BPH). The introduction of the 7-Descarboxamido and 7-Cyano functional groups, along with the benzoate ester moiety, introduces unique pharmacological properties that make this compound a subject of intense study.

The structure of 7-Descarboxamido, 7-Cyano (R)-Silodosin O-Benzoate is meticulously designed to enhance its binding affinity and selectivity for alpha-adrenergic receptors. This specificity is crucial for minimizing side effects and maximizing therapeutic efficacy. The benzoate group, in particular, contributes to the stability and solubility of the compound, which are essential factors for its formulation into viable pharmaceutical products.

Recent advancements in computational chemistry and molecular modeling have allowed researchers to delve deeper into the interactions between 7-Descarboxamido, 7-Cyano (R)-Silodosin O-Benzoate and its target receptors. These studies have revealed that the compound exhibits a high degree of selectivity for alpha-1A adrenergic receptors over alpha-1B and alpha-1D receptors. This selectivity is attributed to the presence of the (R)-configuration at the chiral center, which optimizes the binding geometry and affinity.

In clinical settings, the potential applications of 7-Descarboxamido, 7-Cyano (R)-Silodosin O-Benzoate extend beyond the treatment of BPH. Preliminary studies suggest that this compound may also have utility in managing symptoms associated with overactive bladder syndrome. The enhanced receptor selectivity could lead to improved patient outcomes with fewer systemic side effects compared to existing treatments.

The synthesis of 7-Descarboxamido, 7-Cyano (R)-Silodosin O-Benzoate involves a multi-step process that requires precise control over reaction conditions and stereochemistry. The introduction of the descarboxamido group necessitates careful optimization to ensure high yield and purity. Advanced synthetic methodologies, such as asymmetric hydrogenation and enzymatic resolution, have been employed to achieve the desired enantiomeric purity.

The benzoate ester moiety in the molecule plays a critical role in its pharmacokinetic profile. Esterases in biological systems can hydrolyze this group, releasing free Silodosin or its active metabolites. This metabolic pathway has been studied extensively to understand how it affects the compound's bioavailability and duration of action. Understanding these metabolic processes is essential for formulating effective dosage regimens and predicting potential drug-drug interactions.

Current research is also exploring the potential use of 7-Descarboxamido, 7-Cyano (R)-Silodosin O-Benzoate in combination therapies. For instance, its interaction with other alpha-adrenergic receptor modulators or even non-adrenergic pathways could lead to synergistic effects that enhance therapeutic benefits. Such combination therapies are particularly relevant in complex conditions where multiple physiological pathways are involved.

The safety profile of 7-Descarboxamido, 7-Cyano (R)-Silodosin O-Benzoate is another area of active investigation. Animal models have been utilized to assess acute and chronic toxicity profiles, as well as potential long-term effects on organ systems. These studies are crucial for ensuring that the compound is safe for human use before it advances to clinical trials. The results from these studies will guide dosing strategies and help identify any necessary precautions for patients.

The regulatory landscape for approving new pharmaceuticals like 7-Descarboxamido, 7-Cyano (R)-Silodosin O-Benzoate is stringent and requires comprehensive data on efficacy and safety. Researchers must navigate through various regulatory requirements set by agencies such as the FDA and EMA. The detailed understanding of the compound's mechanism of action, pharmacokinetics, and safety profile will be critical in submitting a robust regulatory submission package.

In conclusion, 7-Descarboxamido, 7-Cyano (R)-Silodosin O-Benzoate represents a significant advancement in the treatment of conditions related to alpha-adrenergic receptor activity. Its unique structure offers enhanced selectivity and potential therapeutic benefits over existing treatments. As research continues to uncover more about its pharmacological properties and interactions with biological systems, this compound holds promise for improving patient care in multiple medical fields.

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