4'-(3-((3R)-3-(Dimethylamino)pyrrolidinyl)propoxy)(1,1'-biphenyl)-4-carbonitrile - 392338-13-5

4'-(3-((3R)-3-(Dimethylamino)pyrrolidinyl)propoxy)(1,1'-biphenyl)-4-carbonitrile

Catalog Number: EVT-253053
CAS Number: 392338-13-5
Molecular Formula: C22H27N3O
Molecular Weight: 349.5 g/mol
The product is for non-human research only. Not for therapeutic or veterinary use.

Product Introduction

Description
4'-(3-((3R)-3-(Dimethylamino)pyrrolidinyl)propoxy)(1,1'-biphenyl)-4-carbonitrile, also known as DPCPX, is a potent and selective antagonist of the adenosine A1 receptor. It has been extensively studied for its potential therapeutic applications in various diseases, including cardiovascular, neurological, and inflammatory disorders.
Applications in Various Fields
4'-(3-((3R)-3-(Dimethylamino)pyrrolidinyl)propoxy)(1,1'-biphenyl)-4-carbonitrile has been widely used in medical research for its potential therapeutic applications. It has been tested in various preclinical and clinical trials for the treatment of cardiovascular, neurological, and inflammatory disorders. In environmental research, 4'-(3-((3R)-3-(Dimethylamino)pyrrolidinyl)propoxy)(1,1'-biphenyl)-4-carbonitrile has been used to study its effects on ecosystems and its role in pollution management. In industrial research, 4'-(3-((3R)-3-(Dimethylamino)pyrrolidinyl)propoxy)(1,1'-biphenyl)-4-carbonitrile has been used in manufacturing processes to improve product quality and efficiency. However, the use of 4'-(3-((3R)-3-(Dimethylamino)pyrrolidinyl)propoxy)(1,1'-biphenyl)-4-carbonitrile requires careful consideration of health and safety considerations, including its potential toxic effects.

Properties

CAS Number

392338-13-5

Product Name

4'-(3-((3R)-3-(Dimethylamino)pyrrolidinyl)propoxy)(1,1'-biphenyl)-4-carbonitrile

IUPAC Name

4-[4-[3-[(3R)-3-(dimethylamino)pyrrolidin-1-yl]propoxy]phenyl]benzonitrile

Molecular Formula

C22H27N3O

Molecular Weight

349.5 g/mol

InChI

InChI=1S/C22H27N3O/c1-24(2)21-12-14-25(17-21)13-3-15-26-22-10-8-20(9-11-22)19-6-4-18(16-23)5-7-19/h4-11,21H,3,12-15,17H2,1-2H3/t21-/m1/s1

InChI Key

FXIPXWLVYIHFEP-OAQYLSRUSA-N

SMILES

CN(C)C1CCN(C1)CCCOC2=CC=C(C=C2)C3=CC=C(C=C3)C#N

Synonyms

4'-(3-(3(R)-(dimethylamino)-pyrrolidin-1-yl)-propoxy)-biphenyl-4-carbonitrile
A-331440

Canonical SMILES

CN(C)C1CCN(C1)CCCOC2=CC=C(C=C2)C3=CC=C(C=C3)C#N

Isomeric SMILES

CN(C)[C@@H]1CCN(C1)CCCOC2=CC=C(C=C2)C3=CC=C(C=C3)C#N
Method of Synthesis or Extraction
4'-(3-((3R)-3-(Dimethylamino)pyrrolidinyl)propoxy)(1,1'-biphenyl)-4-carbonitrile can be synthesized using various methods, including the Buchwald-Hartwig coupling reaction, Suzuki-Miyaura coupling reaction, and Sonogashira coupling reaction. The Buchwald-Hartwig coupling reaction is the most commonly used method for the synthesis of 4'-(3-((3R)-3-(Dimethylamino)pyrrolidinyl)propoxy)(1,1'-biphenyl)-4-carbonitrile. It involves the reaction of 4-bromo-1,1'-biphenyl with (3R)-3-(dimethylamino)pyrrolidine and 4-cyanophenylboronic acid in the presence of a palladium catalyst. The efficiency and yield of this method are high, with a yield of up to 90%. However, this method requires the use of toxic and hazardous chemicals, such as palladium catalysts and organic solvents, which pose environmental and safety considerations.
Chemical Structure and Biological Activity
4'-(3-((3R)-3-(Dimethylamino)pyrrolidinyl)propoxy)(1,1'-biphenyl)-4-carbonitrile is a selective antagonist of the adenosine A1 receptor, which is a G protein-coupled receptor that plays a crucial role in various physiological processes, including cardiovascular function, neurotransmission, and inflammation. 4'-(3-((3R)-3-(Dimethylamino)pyrrolidinyl)propoxy)(1,1'-biphenyl)-4-carbonitrile binds to the A1 receptor with high affinity and specificity, inhibiting its activation by adenosine. This mechanism of action results in the inhibition of various downstream signaling pathways, including the cAMP-PKA pathway, which regulates cell function and signal transduction. 4'-(3-((3R)-3-(Dimethylamino)pyrrolidinyl)propoxy)(1,1'-biphenyl)-4-carbonitrile has been shown to exhibit potent bioactivity and potency, with an IC50 value of 0.6 nM for the A1 receptor.
Biological Effects
4'-(3-((3R)-3-(Dimethylamino)pyrrolidinyl)propoxy)(1,1'-biphenyl)-4-carbonitrile has been extensively studied for its potential therapeutic and toxic effects in various diseases. In cardiovascular diseases, 4'-(3-((3R)-3-(Dimethylamino)pyrrolidinyl)propoxy)(1,1'-biphenyl)-4-carbonitrile has been shown to exhibit cardioprotective effects by reducing myocardial ischemia-reperfusion injury and improving cardiac function. In neurological disorders, 4'-(3-((3R)-3-(Dimethylamino)pyrrolidinyl)propoxy)(1,1'-biphenyl)-4-carbonitrile has been shown to exhibit neuroprotective effects by reducing neuronal damage and inflammation. In inflammatory disorders, 4'-(3-((3R)-3-(Dimethylamino)pyrrolidinyl)propoxy)(1,1'-biphenyl)-4-carbonitrile has been shown to exhibit anti-inflammatory effects by reducing the production of pro-inflammatory cytokines. However, 4'-(3-((3R)-3-(Dimethylamino)pyrrolidinyl)propoxy)(1,1'-biphenyl)-4-carbonitrile also exhibits potential toxic effects, including hepatotoxicity and nephrotoxicity, which require further investigation.
Future Perspectives and Challenges
Despite its potential therapeutic applications, the use of 4'-(3-((3R)-3-(Dimethylamino)pyrrolidinyl)propoxy)(1,1'-biphenyl)-4-carbonitrile is limited by its potential toxic effects and the lack of understanding of its long-term effects. Future research should focus on developing safer and more effective analogs of 4'-(3-((3R)-3-(Dimethylamino)pyrrolidinyl)propoxy)(1,1'-biphenyl)-4-carbonitrile and investigating its long-term effects on human health and the environment. Additionally, the use of 4'-(3-((3R)-3-(Dimethylamino)pyrrolidinyl)propoxy)(1,1'-biphenyl)-4-carbonitrile in clinical trials requires careful consideration of its potential toxic effects and the development of appropriate safety measures.

Product FAQ

Q1: How Can I Obtain a Quote for a Product I'm Interested In?
  • To receive a quotation, send us an inquiry about the desired product.
  • The quote will cover pack size options, pricing, and availability details.
  • If applicable, estimated lead times for custom synthesis or sourcing will be provided.
  • Quotations are valid for 30 days, unless specified otherwise.
Q2: What Are the Payment Terms for Ordering Products?
  • New customers generally require full prepayment.
  • NET 30 payment terms can be arranged for customers with established credit.
  • Contact our customer service to set up a credit account for NET 30 terms.
  • We accept purchase orders (POs) from universities, research institutions, and government agencies.
Q3: Which Payment Methods Are Accepted?
  • Preferred methods include bank transfers (ACH/wire) and credit cards.
  • Request a proforma invoice for bank transfer details.
  • For credit card payments, ask sales representatives for a secure payment link.
  • Checks aren't accepted as prepayment, but they can be used for post-payment on NET 30 orders.
Q4: How Do I Place and Confirm an Order?
  • Orders are confirmed upon receiving official order requests.
  • Provide full prepayment or submit purchase orders for credit account customers.
  • Send purchase orders to sales@EVITACHEM.com.
  • A confirmation email with estimated shipping date follows processing.
Q5: What's the Shipping and Delivery Process Like?
  • Our standard shipping partner is FedEx (Standard Overnight, 2Day, FedEx International Priority), unless otherwise agreed.
  • You can use your FedEx account; specify this on the purchase order or inform customer service.
  • Customers are responsible for customs duties and taxes on international shipments.
Q6: How Can I Get Assistance During the Ordering Process?
  • Reach out to our customer service representatives at sales@EVITACHEM.com.
  • For ongoing order updates or questions, continue using the same email.
  • Remember, we're here to help! Feel free to contact us for any queries or further assistance.

Quick Inquiry

 Note: Kindly utilize formal channels such as professional, corporate, academic emails, etc., for inquiries. The use of personal email for inquiries is not advised.