144217-65-2

Basic information

• Product Name: N1-(2,2,6,6-tetraMethylpiperidin-4-yl)-N2-p-tolyloxalaMide
• Synonyms: N1-(2,2,6,6-tetraMethylpiperidin-4-yl)-N2-p-tolyloxalaMide;Ethanediamide, N1-(4-methylphenyl)-N2-(2,2,6,6-tetramethyl-4-piperidinyl)-;YYA-021;N-(4-Methylphenyl)-N'-(2,2,6,6-tetramethylpiperidin-4-yl)oxalamide;N1-(4-Methylphenyl)-N2-(2,2,6,6-tetramethyl-4-piperidinyl)ethanediamide
• CAS NO: 144217-65-2
• Molecular Formula: C₁₈H₂₇N₃O₂
• Molecular Weight: 317.42588
• EINECS: -0
• Product Categories: Inhibitors
• Mol File: 144217-65-2.mol

Chemical Properties

• Appearance: /
• Density: 1.11±0.1 g/cm3(Predicted)
• Solubility: Limited solubility
• PKA: 11.61±0.70(Predicted)
• CAS DataBase Reference: N1-(2,2,6,6-tetraMethylpiperidin-4-yl)-N2-p-tolyloxalaMide(CAS DataBase Reference)
• NIST Chemistry Reference: N1-(2,2,6,6-tetraMethylpiperidin-4-yl)-N2-p-tolyloxalaMide(144217-65-2)
• EPA Substance Registry System: N1-(2,2,6,6-tetraMethylpiperidin-4-yl)-N2-p-tolyloxalaMide(144217-65-2)

Safety Data

• Hazardous Substances Data: 144217-65-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
N1-(2,2,6,6-tetraMethylpiperidin-4-yl)-N2-p-tolyloxalaMide is used as an HIV entry inhibitor for its ability to block the interaction between the HIV-1 virus and the host's CD4 cells. This interaction is essential for the virus to enter and infect the cells, so by inhibiting this process, YYA-021 can help prevent the spread of HIV within the body.
Used in HIV Research:
In the field of HIV research, N1-(2,2,6,6-tetraMethylpiperidin-4-yl)-N2-p-tolyloxalaMide serves as a valuable tool for studying the mechanisms of HIV entry into host cells. Understanding these mechanisms can lead to the development of new therapeutic strategies and improved treatments for HIV and AIDS.
Used in Drug Development:
N1-(2,2,6,6-tetraMethylpiperidin-4-yl)-N2-p-tolyloxalaMide is also used in the development of new antiviral drugs. Its unique mechanism of action as a CD4 mimic offers a potential alternative to traditional antiretroviral therapies, which may be less effective in certain cases or have undesirable side effects. By studying and optimizing the properties of YYA-021, researchers can potentially create more effective and targeted treatments for HIV.

Biological Activity

yya-021 is a small-molecule cd4 mimic that inhibits hiv entry [1].cd4 is a cell surface protein. the entry of human immunodeficiency virus type 1 (hiv-1) into target cells is initiated by the interaction of cd4 and viral envelope glycoprotein gp120. cd4 mimic inhibits the interaction between gp120 and cd4 and then inhibits hiv entry [1].yya-021 is a small-molecule cd4 mimic that inhibits hiv entry. yya-021 competitively inhibited gp120-cd4 interaction [1]. in tzm-bl cells infected with simian-human immunodeficiency virus isolate mna (shiv mna) or hiv-1 mna pseudotyped viruses, yya-021 inhibited the entry of envs of shiv mna and hiv-1. kd-247 (the anti-v3 loop mab, 50 μg) caused 50% neutralization of hiv-1 mna. however, in the presence of 20 μm of yya-021, kd-247 (<0.05 μg) caused 50% neutralization of hiv-1 mna, which suggested that the synergistic neutralization effect of yya-021 and kd-247. in the presence of yya-021, shiv mna became more sensitive to igg [2].in jcl:sd rats, the maximum tolerated dose of yya-021.hcl was 2.5 mg. when administrated by tail vein injection, yya-021 exhibited widespread tissue distribution due to its hydrophobicity. in a rhesus macaque, the maximum tolerated dose of yya-021.hcl was 35.3 mg [1].

references

[1]. hashimoto c, narumi t, otsuki h, et al. a cd4 mimic as an hiv entry inhibitor: pharmacokinetics. bioorg med chem, 2013, 21(24): 7884-7889. [2]. otsuki h, hishiki t, miura t, et al. generation of a replication-competent simian-human immunodeficiency virus, the neutralization sensitivity of which can be enhanced in the presence of a small-molecule cd4 mimic. j gen virol, 2013, 94(pt 12): 2710-2716.

Upstream product

• 36768-62-4 4-AMINO-2,2,6,6-TETRAMETHYLPIPERIDINE 
• 42868-89-3 2-oxo-2-(p-tolylamino)acetic acid 
• 106-49-0 p-toluidine 
• 18522-98-0 ethyl 2-[(4-methylphenyl)amino]-2-oxoacetate 

Relevant articles and documents

2,2,2-Trifluoroethyl Chlorooxoacetate-Universal Reagent for One-Pot Parallel Synthesis of N1-Aryl-N2-alkyl-Substituted Oxamides

A one-pot parallel synthesis of N1-aryl-N2-alkyl-substituted oxamides with 2,2,2-trifluoroethyl chlorooxoacetate was developed. The synthesis of a library of 45 oxamides revealed higher efficiency of this reagent over the known ethyl chlorooxoacetate. The reagent was successfully used to prepare the known oxamide-containing HIV entry inhibitors.

CD4 mimics targeting the mechanism of HIV entry

A structure-activity relationship study was conducted of several CD4 mimicking small molecules which block the interaction between HIV-1 gp120 and CD4. These CD4 mimics induce a conformational change in gp120, exposing its co-receptor-binding site. This induces a highly synergistic interaction in the use in combination with a co-receptor CXCR4 antagonist and reveals a pronounced effect on the dynamic supramolecular mechanism of HIV-1 entry.