4-Hydroxy thalidomide - 5054-59-1

4-Hydroxy thalidomide

Catalog Number: EVT-255452
CAS Number: 5054-59-1
Molecular Formula: C₁₃H₁₀N₂O₅
Molecular Weight: 274.23 g/mol
The product is for non-human research only. Not for therapeutic or veterinary use.
Price:

Product Introduction

Description
4-Hydroxy thalidomide is a derivative of thalidomide, a drug that was initially developed as a sedative but was later found to have immunomodulatory and anti-inflammatory properties. 4-Hydroxy thalidomide is a more potent analog of thalidomide and has been extensively studied for its therapeutic potential in various diseases.
Applications in Various Fields
In medical research, 4-Hydroxy thalidomide has played a significant role in drug development. It has been used as a lead compound for the development of more potent analogs, such as lenalidomide and pomalidomide, which are currently used in the treatment of multiple myeloma and other diseases. Clinical trials have shown promising results for the use of 4-Hydroxy thalidomide in the treatment of leprosy and inflammatory bowel disease. However, its potential side effects, such as teratogenicity, must be carefully considered. In environmental research, 4-Hydroxy thalidomide has been studied for its effects on ecosystems and its role in pollution management. It has been shown to have a low environmental impact and can be used as a sustainable alternative to other chemicals. In industrial research, 4-Hydroxy thalidomide has been used in manufacturing processes to improve product quality and efficiency. Health and safety considerations must be taken into account when using 4-Hydroxy thalidomide in industrial settings.

Properties

CAS Number

5054-59-1

Product Name

4-Hydroxy thalidomide

IUPAC Name

2-(2,6-dioxopiperidin-3-yl)-4-hydroxyisoindole-1,3-dione

Molecular Formula

C₁₃H₁₀N₂O₅

Molecular Weight

274.23 g/mol

InChI

InChI=1S/C13H10N2O5/c16-8-3-1-2-6-10(8)13(20)15(12(6)19)7-4-5-9(17)14-11(7)18/h1-3,7,16H,4-5H2,(H,14,17,18)

InChI Key

XMPJICVFSDYOEG-UHFFFAOYSA-N

SMILES

C1CC(=O)NC(=O)C1N2C(=O)C3=C(C2=O)C(=CC=C3)O

Synonyms

5054-59-1; 4-Hydroxy thalidomide; E3 ligase Ligand 2; Thalidomide-OH; Cereblon ligand 2; 2-(2,6-dioxopiperidin-3-yl)-4-hydroxyisoindoline-1,3-dione

Canonical SMILES

C1CC(=O)NC(=O)C1N2C(=O)C3=C(C2=O)C(=CC=C3)O
Method of Synthesis or Extraction
4-Hydroxy thalidomide can be synthesized by various methods, including the reaction of thalidomide with hydroxylamine, the oxidation of thalidomide with potassium permanganate, and the reduction of thalidomide with sodium borohydride. The efficiency and yield of each method vary, with the hydroxylamine method being the most efficient and yielding the highest amount of 4-Hydroxy thalidomide. However, the use of hydroxylamine requires careful handling due to its toxicity. The oxidation method is less efficient and yields a lower amount of 4-Hydroxy thalidomide, but it is a safer method. The reduction method is also less efficient and yields a lower amount of 4-Hydroxy thalidomide, but it is a more environmentally friendly method.
Chemical Structure and Biological Activity
The chemical structure of 4-Hydroxy thalidomide is similar to that of thalidomide, with the addition of a hydroxyl group at the 4-position of the phthalimide ring. The hydroxyl group enhances the potency of 4-Hydroxy thalidomide compared to thalidomide. The mechanism of action of 4-Hydroxy thalidomide is not fully understood, but it is known to have immunomodulatory, anti-inflammatory, and anti-angiogenic properties. It has been shown to inhibit the production of tumor necrosis factor-alpha (TNF-α) and other pro-inflammatory cytokines, as well as to enhance the activity of natural killer cells and T cells.
Biological Effects
4-Hydroxy thalidomide has been shown to have various biological effects on cell function and signal transduction. It has been shown to induce apoptosis in cancer cells, inhibit angiogenesis, and modulate the immune response. However, it also has potential toxic effects, including teratogenicity and neurotoxicity. In terms of therapeutic effects, 4-Hydroxy thalidomide has been studied for its potential in the treatment of various diseases, including multiple myeloma, leprosy, and inflammatory bowel disease.
Future Perspectives and Challenges
Despite its potential therapeutic benefits, the use of 4-Hydroxy thalidomide is limited by its potential toxic effects. Future research should focus on developing safer analogs with fewer side effects. Additionally, the mechanism of action of 4-Hydroxy thalidomide should be further elucidated to better understand its therapeutic potential. The use of 4-Hydroxy thalidomide in combination with other drugs should also be explored to enhance its efficacy. Finally, the challenges of using 4-Hydroxy thalidomide in clinical settings, such as patient compliance and cost, must be addressed to ensure its widespread use.
Conclusion:
4-Hydroxy thalidomide is a potent analog of thalidomide with immunomodulatory, anti-inflammatory, and anti-angiogenic properties. It has been extensively studied for its therapeutic potential in various diseases, including multiple myeloma, leprosy, and inflammatory bowel disease. However, its potential toxic effects, such as teratogenicity and neurotoxicity, must be carefully considered. Future research should focus on developing safer analogs with fewer side effects and exploring the use of 4-Hydroxy thalidomide in combination with other drugs.

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.