5-(4-cyanophenoxy)-2,3-dihydro-1-hydroxy-2,1-benzoxaborole

Base Information

• Chemical Name: 5-(4-cyanophenoxy)-2,3-dihydro-1-hydroxy-2,1-benzoxaborole
• CAS No.: 906673-24-3
• Molecular Formula: C14H10BNO3
• Molecular Weight: 251.049
• Hs Code.: 2926909090
• Mol file: 906673-24-3.mol

Synonyms:AN2728; 4-[(1,3-Dihydro-1-hydroxy-2,1-benzoxaborol-5-yl)oxy]benzonitrile

Chemical Property of 5-(4-cyanophenoxy)-2,3-dihydro-1-hydroxy-2,1-benzoxaborole

Chemical Property:

• Boiling Point: 425.9±55.0 °C(Predicted)
• PKA: 7.00±0.20(Predicted)
• PSA: 62.48000
• Density: 1.33±0.1 g/cm3(Predicted)
• LogP: 1.56828
• Storage Temp.: room temp
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

99% ^*data from raw suppliers

Crisaborole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: Crisaborole is a phosphodiesterase- 4 (PDE4) inhibitor that was approved by the USFDA for the treatment of mild to moderate atopic dermatitis (AD) in patients aged two years and older. The drug, which was developed by Anacor Pharmaceuticals and later acquired and marketed by Pfizer, is delivered as a 2% ointment, which is applied topically. The unique employment of boron within the chemical structure of the drug is designed to enable selective engagement of PDE4 (an enzyme involved in the conversion of cAMP into AMP, which signals for downstream inflammatory events), effective penetration of the drug through human skin, and rapid clearance to limit systemic circulation. AN2728 is a boron-based, topical anti-inflammatory agent that inhibits phosphodiesterase 4 (PDE4; IC50 = 0.11 μM). It is less potent against PDE1A, PDE3A, and PDE7A (IC50s = 6.12, 6.41, and 0.73 μM, respectively). AN2728 suppresses the release of the proinflammatory cytokines TNF-α, IL-2, INF-γ, IL-5, and IL-10 with IC50 values of 0.50, 0.59, 0.72, 2.25, and 2.58 μM, respectively.
• Uses: A series of phenoxy benzoxaboroles were synthesized and screened for their inhibitory activity against PDE4 and cytokine release. 5-?(4-?Cyanophenoxy)?-?2,?3-?dihydro-?1-?hydroxy-?2,?1-?benzoxaborole (AN2728) showed potent activity both in vitro and in vivo. AN2728 is being studied as an anti-inflammatory agent.

Technology Process of 5-(4-cyanophenoxy)-2,3-dihydro-1-hydroxy-2,1-benzoxaborole

There total 94 articles about 5-(4-cyanophenoxy)-2,3-dihydro-1-hydroxy-2,1-benzoxaborole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

1,3-dihydro-1,5-dihydroxy-2,1-benzoxaborolane (1187190-70-0) + 4-fluorobenzonitrile (1194-02-1,143234-87-1) → AN2728 (906673-24-3)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 110 ℃; for 12h; Reagent/catalyst; Temperature;

Reference yield: 95.0%

4-Cyanochlorobenzene (623-03-0) + 1,3-dihydro-1,5-dihydroxy-2,1-benzoxaborolane (1187190-70-0) → AN2728 (906673-24-3)

Guidance literature:

With caesium carbonate; In dimethyl sulfoxide; at 60 ℃; Reagent/catalyst; Temperature; Solvent;

Reference yield: 93.3%

1,3-dihydro-1,5-dihydroxy-2,1-benzoxaborolane (1187190-70-0) + 4-bromobenzenecarbonitrile (623-00-7) → AN2728 (906673-24-3)

Guidance literature:

With caesium carbonate; In dimethyl sulfoxide; at 60 ℃; Reagent/catalyst; Solvent; Temperature;

upstream raw materials:

water

4-Cyanochlorobenzene

1,3-dihydro-1,5-dihydroxy-2,1-benzoxaborolane

4-bromobenzenecarbonitrile

Downstream raw materials:

5-(4-(1H-tetrazol-5-yl)phenoxy)benzo[c][1,2]oxaborol-1(3H)-ol

4-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-5-yloxy)benzoic acid methyl ester