C(Cbz)-acetic acid
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C(Cbz)-acetic acid

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Category
CBZ-Amino Acids
Catalog number
BAT-008365
CAS number
144564-95-4
Molecular Formula
C14H13N3O5
Molecular Weight
303.27
IUPAC Name
2-[2-oxo-4-(phenylmethoxycarbonylamino)pyrimidin-1-yl]acetic acid
Synonyms
2-Oxo-4-[(benzyloxycarbonyl)amino]pyrimidine-1(2H)-acetic acid
Density
1.39±0.1 g/cm3
Melting Point
272-274 °C
InChI
InChI=1S/C14H13N3O5/c18-12(19)8-17-7-6-11(15-13(17)20)16-14(21)22-9-10-4-2-1-3-5-10/h1-7H,8-9H2,(H,18,19)(H,15,16,20,21)
InChI Key
ONHBSJOXWOGKOD-UHFFFAOYSA-N
Canonical SMILES
C1=CC=C(C=C1)COC(=O)NC2=NC(=O)N(C=C2)CC(=O)O
1. Ellagic acid enhances the antinociceptive action of carbamazepine in the acetic acid writhing test with mice
Bahareh Naghizadeh, Mohammad Taghi Mansouri, Behnam Ghorbanzadeh Pharm Biol. 2016;54(1):157-61. doi: 10.3109/13880209.2015.1025288. Epub 2015 Apr 21.
Context: Ellagic acid (EA) produced antinociceptive and anti-inflammatory effects through the central and peripheral sites of action. Objective: The objective of the current study was to examine the functional interaction between ellagic acid and carbamazepine (CBZ) on pain. Materials and methods: Fourteen groups of mice (8-10 each) were used in this study. Pain was induced by intraperitoneal acetic acid in mice (writhing test) and the functional interaction was analyzed using the isobolographic method. EA at doses 0.3, 1, 3, and 10 mg/kg and carbamazepine at doses 3, 10, 20, and 30 mg/kg, alone and also in combination (1/2, 1/4, and 1/8 of the drug's ED50) were intraperitoneally administered 30 min before acetic acid (0.6% v/v). Then, the abdominal writhes were counted during a 25-min period. Results: EA (0.3-10 mg/kg, i.p.) and CBZ (3-30 mg/kg, i.p.) inhibited the writhing response evoked by acetic acid. Fifty percent effective dose (ED50) values against this tonic pain were 1.02 mg/kg and 6.40 mg/kg for EA and CBZ, respectively. The antinociception induced by EA showed higher potency than that of carbamazepine. Co-administration of increasing fractional increments of ED50 values of EA and CBZ produced additive interaction against writhing responses, as revealed by isobolographic analysis. Discussion and conclusion: These results suggest that a combination of carbamazepine and ellagic acid may be a new strategy for the management of neuropathic pain such as what occurs in trigeminal neuralgia, since the use of carbamazepine is often limited by its adverse effects and by reduction of its analgesic effect through microsomal enzyme induction.
2. Highly efficient activation of peracetic acid by nano-CuO for carbamazepine degradation in wastewater: The significant role of H2O2 and evidence of acetylperoxy radical contribution
Longlong Zhang, Jiabin Chen, Yalei Zhang, Yao Xu, Tinglu Zheng, Xuefei Zhou Water Res. 2022 Jun 1;216:118322. doi: 10.1016/j.watres.2022.118322. Epub 2022 Mar 19.
Peracetic acid (PAA)-based advanced oxidation processes (AOPs) has attracted increasing attentions towards contaminant degradation in the wastewater treatment. Herein, we report the efficient activation of PAA by nano-CuO (nCuO/PAA) to degrade carbamazepine (CBZ) for the first time. Rapid degradation of CBZ was observed in the nCuO/PAA system at neutral initial pH. A new scavenging experiment with Mn2+ as a specific scavenger was developed to distinguish the dominant role of CH3C(O)OO● for CBZ degradation in the nCuO/PAA process. The oxidation of CBZ by CH3C(O)OO● was verified to proceed via the electrons transfer, and the acute and chronic toxicity of the transformation products was significantly reduced. The efficient activation of PAA by nCuO was found to be realized through continuous conversion of Cu(II) to Cu(I), which was significantly boosted by co-existing H2O2. The nCuO/PAA process was slightly affected by the water matrices, and maintained high efficiency in real water samples. The findings obtained in this study provide new insights into the catalytic formation of CH3C(O)OO● from PAA and facilitate the development and application of PAA-based AOPs in wastewater treatment.
3. Tertiary treatment of urban wastewater by solar and UV-C driven advanced oxidation with peracetic acid: Effect on contaminants of emerging concern and antibiotic resistance
Luigi Rizzo, Teresa Agovino, Samira Nahim-Granados, María Castro-Alférez, Pilar Fernández-Ibáñez, María Inmaculada Polo-López Water Res. 2019 Feb 1;149:272-281. doi: 10.1016/j.watres.2018.11.031. Epub 2018 Nov 14.
Photo-driven advanced oxidation process (AOP) with peracetic acid (PAA) has been poorly investigated in water and wastewater treatment so far. In the present work its possible use as tertiary treatment of urban wastewater to effectively minimize the release into the environment of contaminants of emerging concern (CECs) and antibiotic-resistant bacteria was investigated. Different initial PAA concentrations, two light sources (sunlight and UV-C) and two different water matrices (groundwater (GW) and wastewater (WW)) were studied. Low PAA doses were found to be effective in the inactivation of antibiotic resistant Escherichia coli (AR E. coli) in GW, with the UV-C process being faster (limit of detection (LOD) achieved for a cumulative energy (QUV) of 0.3 kJL-1 with 0.2 mg PAA L-1) than solar driven one (LOD achieved at QUV = 4.4 kJL-1 with 0.2 mg PAA L-1). Really fast inactivation rates of indigenous AR E. coli were also observed in WW. Higher QUV and PAA initial doses were necessary to effectively remove the three target CECs (carbamazepine (CBZ), diclofenac and sulfamethoxazole), with CBZ being the more refractory one. In conclusion, photo-driven AOP with PAA can be effectively used as tertiary treatment of urban wastewater but initial PAA dose should be optimized to find the best compromise between target bacteria inactivation and CECs removal as well as to prevent scavenging effect of PAA on hydroxyl radicals because of high PAA concentration.
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