4-[8-(2,1,3-Benzoxadiazol-5-yl)-1,7-naphthyridin-6-yl]benzoic acid

Base Information

• Chemical Name: 4-[8-(2,1,3-Benzoxadiazol-5-yl)-1,7-naphthyridin-6-yl]benzoic acid
• CAS No.: 426268-06-6
• Molecular Formula: C21H12N4O3
• Molecular Weight: 368.34500
• DSSTox Substance ID: DTXSID50430919
• Nikkaji Number: J1.676.694A
• Wikidata: Q82244669
• Pharos Ligand ID: 5HWJWRNY7MUR
• ChEMBL ID: CHEMBL77826
• Mol file: 426268-06-6.mol

Synonyms:4-(8-benzo(1,2,5)oxadiazol-5-yl-(1,7)naphthyridin-6-yl)benzoic acid;NVP ABE171;NVP-ABE171;NVPABE171

Chemical Property of 4-[8-(2,1,3-Benzoxadiazol-5-yl)-1,7-naphthyridin-6-yl]benzoic acid

Chemical Property:

• Boiling Point: 592.4±60.0 °C(Predicted)
• PKA: 3.87±0.10(Predicted)
• PSA: 102.00000
• Density: 1.436±0.06 g/cm3(Predicted)
• LogP: 4.19820
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 3
• Exact Mass: 368.09094026
• Heavy Atom Count: 28
• Complexity: 568

Purity/Quality:

≥95% ^*data from raw suppliers

4-[8-(2,1,3-Benzoxadiazol-5-yl)-1,7-naphthyridin-6-yl]benzoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=CC(=NC(=C2N=C1)C3=CC4=NON=C4C=C3)C5=CC=C(C=C5)C(=O)O
• Uses: 4-[8-(2,1,3-Benzoxadiazol-5-yl)-1,7-naphthyridin-6-yl]benzoic Acid is a phosphodiesterase PDE4D inhibitor that functions as an anti-prostrate cancer therapy in both in vitro and in vivo models. Also functions as phosphodiesterase 4 inhibitor with anti-inflammatory activity with the potential for the treatment of airway inflammatory conditions such as asthma and chronic obstructive pulmonary diseases.

Technology Process of 4-[8-(2,1,3-Benzoxadiazol-5-yl)-1,7-naphthyridin-6-yl]benzoic acid

There total 15 articles about 4-[8-(2,1,3-Benzoxadiazol-5-yl)-1,7-naphthyridin-6-yl]benzoic acid 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: 68.0%

4-carboxyphenylboronic acid (14047-29-1) + trifluoro-methanesulfonic acid 8-benzo[1,2,5]oxadiazol-5-yl-[1,7]naphthyridin-6-yl ester (426268-11-3) → RO-458,2640 (426268-06-6)

Guidance literature:

With sodium carbonate; triphenylphosphine; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In N,N-dimethyl-formamide; at 80 ℃; for 2h;

DOI:10.1016/S0960-894X(01)00720-X

Reference yield:

benzo[c][1,2,5]oxadiazole-5-boronic acid (426268-09-9) + 6-(4-carboxyphenyl)-8-bromo-1,7-naphthyridine (207279-31-0) → RO-458,2640 (426268-06-6)

Guidance literature:

With sodium carbonate; tris-(o-tolyl)phosphine; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In N,N-dimethyl-formamide; at 110 ℃; for 2h;

DOI:10.1016/S0960-894X(01)00720-X

Reference yield:

5-bromo-benzo[1,2,5]oxadiazole (51376-06-8) → RO-458,2640 (426268-06-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 45 percent / n-BuLi; TMEDA; B(OEt)3 / tetrahydrofuran; pentane / 0.08 h / -100 °C

2: Pd(dba)2; P(o-tol)3; 2 N aq. Na₂CO₃ / dimethylformamide; toluene / 3 h / 110 °C

3: 40 percent / NaNO₂ / dimethylformamide / 3 h / 20 °C

4: 68 percent / Pd(dba)2; PPh₃; 2 N aq. Na₂CO₃ / dimethylformamide / 2 h / 80 °C

With n-butyllithium; triethyl borate; N,N,N,N,-tetramethylethylenediamine; sodium carbonate; triphenylphosphine; tris-(o-tolyl)phosphine; bis(dibenzylideneacetone)-palladium⁽⁰⁾; sodium nitrite; In tetrahydrofuran; N,N-dimethyl-formamide; toluene; pentane; 2: Suzuki-type coupling / 4: Suzuki-type coupling;

DOI:10.1016/S0960-894X(01)00720-X

upstream raw materials:

4-carboxyphenylboronic acid

trifluoro-methanesulfonic acid 8-benzo[1,2,5]oxadiazol-5-yl-[1,7]naphthyridin-6-yl ester

benzo[c][1,2,5]oxadiazole-5-boronic acid

6-(4-carboxyphenyl)-8-bromo-1,7-naphthyridine

Refernces