320347-97-5

Basic information

• Product Name: 2-Thiopheneacetic acid, α-hydroxy-α-2-thienyl-, (3R)-1-azabicyclo[2.2.2]oct-3-yl ester
• Synonyms: 2-Thiopheneacetic acid, α-hydroxy-α-2-thienyl-, (3R)-1-azabicyclo[2.2.2]oct-3-yl ester;(R)-Quinucldin-3-yl hydroxybis(2-thienyl)acetate;2-Thiopheneacetic acid, α-hydroxy-α-2-thienyl-, (3R)-1-azabicyclo[2.2.2]oct-3-yl ester-5;GYDFTKNRHZMENP-ZDUSSCGKSA-N
• CAS NO: 320347-97-5
• Molecular Formula: C₁₇H₁₉NO₃S₂
• Molecular Weight: 349.46766
• Mol File: 320347-97-5.mol
• Article Data: 19

Chemical Properties

• Melting Point: 180℃ (isopropyl ether )
• Boiling Point: 513.3±50.0 °C(Predicted)
• Appearance: /
• Density: 1.40±0.1 g/cm3(Predicted)
• PKA: 10.33±0.29(Predicted)
• CAS DataBase Reference: 2-Thiopheneacetic acid, α-hydroxy-α-2-thienyl-, (3R)-1-azabicyclo[2.2.2]oct-3-yl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Thiopheneacetic acid, α-hydroxy-α-2-thienyl-, (3R)-1-azabicyclo[2.2.2]oct-3-yl ester(320347-97-5)
• EPA Substance Registry System: 2-Thiopheneacetic acid, α-hydroxy-α-2-thienyl-, (3R)-1-azabicyclo[2.2.2]oct-3-yl ester(320347-97-5)

Safety Data

• Hazardous Substances Data: 320347-97-5(Hazardous Substances Data)

Usage

Uses

(R)-3-Quinuclidinyl di(2-thienyl)glycolate acts as a potent and long-acting muscarinic antagonist with minimal systemic exposure after inhalation. Used in the treatment of chronic obstructive pulmonary disease.

Upstream product

• 1003-09-4 2-bromothiophene 
• 4746-63-8 2-hydroxy-2,2-di(thiophen-2-yl)acetic acid 
• 25333-42-0 (R)-quinuclidin-3-ol 
• 27998-36-3 2,2-di(2-thiophenyl)-2-hydroxyethanoic acid-3-quinine ester 
• 1619-34-7 3-quinuclidinol 
• 26447-85-8 hydroxy-di-thiophen-2-yl-acetic acid methyl ester 
• 59653-40-6 (+)-Aceclidine 
• 28569-88-2 Ethyl (2,2'-Dithienyl)glycolate 

Downstream Products

• 1195981-90-8 (R)-3-(2-hydroxy-2,2-dithiophen-2-yl-acetoxy)-1-(5-phenylisoxazol-3-ylmethyl)-1-azoniabicyclo[2.2.2]octane chloride 
• 867022-63-7 aclidinium bromide 
• 320345-88-8 (3R)-3-{[hydroxy(di-2-thienyl)acetyl]oxy}-1-(2-phenylethyl)-1-azoniabicyclo[2.2.2]octane bromide 
• 1185907-26-9 (3R)-1-benzyl-3-{[hydroxy(di-2-thienyl)acetyl]oxy}-1-azoniabicyclo[2.2.2]octane bromide 
• 320345-91-3 (3R)-3-{[hydroxy(di-2-thienyl)acetyl]oxy}-1-(4-phenylbutyl)-1-azoniabicyclo[2.2.2]octane bromide 
• 320345-99-1 aclidinium bromide 

Relevant articles and documents

Choline M receptor anti-caking agent re-crystallization method

The invention provides a choline M receptor anti-caking agent re-crystallization method, which comprises: (1) heating an aclidinium bromide crude product and DMF to a temperature of 90-130 DEG C, stirring, dissolving, and clarifying; (2) cooling the solut

Novel method for synthesis and purification of aclidinium bromide

The invention discloses a novel method for synthesis and purification of aclidinium bromide. According to the method, tetrahydrofuran is used, haloalkane is used as an initiator, and a finished product is obtained through solvent extraction and recrystall

Discovery of Novel Potent Muscarinic M3 Receptor Antagonists with Proper Plasma Stability by Structural Recombination of Marketed M3 Antagonists

The marketed long-acting M3 antagonists for treatment of chronic obstructive pulmonary disease have inappropriate plasma stability (either overstable or excessively unstable), which causes substantial systemic exposure or poor patient compliance. To discover novel M3 antagonists with proper plasma stability, we synthesized and biologically evaluated a series of chiral quaternary ammonium salts of pyrrolidinol esters, which were designed by structural recombination of the marketed M3 antagonists. As a result, two novel potent M3 antagonists, (R/S)-3-[2-hydroxy-2,2-di(thiophen-2-yl)acetoxy]-1,1-dimethylpyrrolidinium bromides (1 a: Ki=0.16 nm, IC50=0.38 nm, t1/2=9.34 min; 1 b: Ki=0.32 nm, IC50=1.01 nm, t1/2=19.2 min) with proper plasma stability were identified, which (particularly 1 a) hold great promise as clinical drug candidates to overcome the drawbacks caused by the inappropriate stability of the currently marketed M3 antagonists. In addition, structure–activity relationship studies revealed that the R configuration of the pyrrolidinyl C3 atom was clearly better than the S configuration.