702631-29-6

Basic information

• Product Name: (2-phenyl-3H-imidazol-4-yl)-acetic acid
• Synonyms: (2-phenyl-3H-imidazol-4-yl)-acetic acid
• CAS NO: 702631-29-6
• Molecular Weight: 202.213
• Mol File: 702631-29-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2-phenyl-3H-imidazol-4-yl)-acetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2-phenyl-3H-imidazol-4-yl)-acetic acid(702631-29-6)
• EPA Substance Registry System: (2-phenyl-3H-imidazol-4-yl)-acetic acid(702631-29-6)

Safety Data

• Hazardous Substances Data: 702631-29-6(Hazardous Substances Data)

Upstream product

• 57118-89-5 5-chloromethyl-2-phenyl-1H-imidazole 
• 43002-54-6 5-hydroxymethyl-2-phenyl-1H-imidazole 
• 618-39-3 benzamidin 
• 52353-66-9 2-(2-phenyl-1H-imidazol-5-yl)acetonitrile 

Relevant articles and documents

Highly potent geminal bisphosphonates. From pamidronate disodium (Aredia) to zoledronic acid (Zometa)

Bisphosphonates (BPs) are pyrophosphate analogues in which the oxygen in P-O-P has been replaced by a carbon, resulting in a metabolically stable P-C-P structure. Pamidronate (1b, Novartis), a second-generation BP, was the starting point for extensive SAR studies. Small changes of the structure of pamidronate lead to marked improvements of the inhibition of osteoclastic resorption potency. Alendronate (1c, MSD), with an extra methylene group in the N-alkyl chain, and olpadronate (1h, Gador), the N,N-dimethyl analogue, are about 10 times more potent than pamidronate. Extending one of the N-methyl groups of olpadronate to a pentyl substituent leads to ibandronate (1k, Roche, Boehringer-Mannheim), which is the most potent close analogue of pamidronate. Even slightly better antiresorptive potency is achieved with derivatives having a phenyl group linked via a short aliphatic tether of three to four atoms to nitrogen, the second substituent being preferentially a methyl group (e.g., 4g, 4j, 5d, or 5r). The most potent BPs are found in the series containing a heteroaromatic moiety (with at least one nitrogen atom), which is linked via a single methylene group to the geminal bisphosphonate unit. Zoledronic acid (6i), the most potent derivative, has an ED50 of 0.07 mg/kg in the TPTX in vivo assay after sc administration. It not only shows by far the highest therapeutic ratio when comparing resorption inhibition with undesired inhibition of bone mineralization but also exhibits superior renal tolerability. Zoledronic acid (6i) has thus been selected for clinical development under the registered trade name Zometa. The results of the clinical trials indicate that low doses are both efficacious and safe for the treatment of tumor-induced hypercalcemia, Paget's disease of bone, osteolytic metastases, and postmenopausal osteoporosis.