N-Benzoyl-L-glutamine
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| Category | Others |
| Catalog number | BBF-05219 |
| CAS | 14307-83-6 |
| Molecular Weight | 250.25 |
| Molecular Formula | C12H14N2O4 |
| Purity | >95% by HPLC |
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Specification
| Related CAS | 294856-87-4 (D-configuration) |
| Synonyms | L-Glutamine, N2-benzoyl-; Bz-L-Gln-OH; N2-Benzoyl-L-glutamine; benzoyl-L-glutamine |
| Storage | Store at -20°C |
| IUPAC Name | (2S)-5-amino-2-benzamido-5-oxopentanoic acid |
| Canonical SMILES | C1=CC=C(C=C1)C(=O)NC(CCC(=O)N)C(=O)O |
| InChI | InChI=1S/C12H14N2O4/c13-10(15)7-6-9(12(17)18)14-11(16)8-4-2-1-3-5-8/h1-5,9H,6-7H2,(H2,13,15)(H,14,16)(H,17,18)/t9-/m0/s1 |
| InChI Key | WSDWRFQYFHCSDA-VIFPVBQESA-N |
Properties
| Boiling Point | 649.0±50.0°C (Predicted) |
| Melting Point | 140-142°C |
| Density | 1.306±0.06 g/cm3 (Predicted) |
Reference Reading
1. [Synthesis of diethyl N-[p-(methylamino)benzoyl]-L-glutamate]
Chao Tian, Shou-xin Zhou, Biao Wang, Xi-ling Deng, Ying Guo, Zhi-li Zhang, Xiao-wei Wang, Jun-yi Liu Beijing Da Xue Xue Bao Yi Xue Ban. 2008 Aug 18;40(4):443-5.
Objective: To find a best synthesis method of diethyl N-[p-(methylamino)benzoyl]-L-glutamate(1). Methods: Using diethyl N-(p- aminobenzoyl)-L-glutamate (2) as a starting material via a one-pot process of benzylation and methylation, the diethyl N-[p-(methylamino)benzoyl ]-L-glutamate (3) is prepared in high yield. Then compound 1 was conveniently obtained from debenzylation of compound 3 by Pd/C. Results: The target compound was obtained through 2-step reaction in 88% overall yield in only 6 h, and its structure was identified by 1HNMR and MS. Conclusion: It is a convenient and efficient method of preparation of diethyl N-[p-(methylamino)benzoyl]-L-glutamate.
2. [Improved synthesis process of diethyl N-[4-[(2,4-diaminopyrido[3,2-d]pyrimidin-6-yl)methylamino]benzoyl]-L-glutamate]
Xin Liu, Yi-qing Du, Yuan-xin Li, Meng Wang, Zhi-li Zhang, Xiao-wei Wang, Jun-yi Liu, Chao Tian Beijing Da Xue Xue Bao Yi Xue Ban. 2015 Oct 18;47(5):842-5.
Objective: To establish a new approach to synthesis of diethyl N-[4-[(2,4-diaminopyrido[3,2-d]pyrimidin-6-yl)methylamino]benzoyl]-L-glutamate. Methods: Target compound (5) was synthesized by the use of (2,4-dioxo-tetrahydropyridopyrimidin-6-yl)methyl acetate (1) as starting material via hydrolysis, chlorination, condensation with diethyl (p-aminobenzoyl)glutamate and aminolysis. Results: A new approach to synthesis of diethyl N-[4-[(2,4-diaminopyrido[3,2-d]pyrimidin-6-yl)methylamino]benzoyl]-L-glutamate was established. This synthetic route has hydrolysis reaction, chlorination, diethyl N-(p-aminobenzoyl)-L-glutamate condensation reaction and ammonolysis reaction. The total yield is 36.7%.The structures of those compounds have identified by 1H nuclear magnetic resonance, 13C nuclear magnetic resonance and mass spectrometry. This synthetic route avoid the unstable brominated reaction product and improves the harsh condition of ammonolysis reaction. Conclusion: The new synthetic route has improved the reaction condition and the stability of the intermediate, and increased the extent of the derivative compounds, which has great significance to anti-folic acid of anti-tumor inhibitor synthesis.
3. Development and binding mode assessment of N-[4-[2-propyn-1-yl[(6S)-4,6,7,8-tetrahydro-2-(hydroxymethyl)-4-oxo-3H-cyclopenta[g]quinazolin-6-yl]amino]benzoyl]-l-γ-glutamyl-D-glutamic acid (BGC 945), a novel thymidylate synthase inhibitor that targets tumor cells
Anna Tochowicz, Sean Dalziel, Oliv Eidam, Joseph D O'Connell rd, Sarah Griner, Janet S Finer-Moore, Robert M Stroud J Med Chem. 2013 Jul 11;56(13):5446-55. doi: 10.1021/jm400490e. Epub 2013 Jun 21.
N-[4-[2-Propyn-1-yl[(6S)-4,6,7,8-tetrahydro-2-(hydroxymethyl)-4-oxo-3H-cyclopenta[g]quinazolin-6-yl]amino]benzoyl]-l-γ-glutamyl-d-glutamic acid 1 (BGC 945, now known as ONX 0801), is a small molecule thymidylate synthase (TS) inhibitor discovered at the Institute of Cancer Research in London. It is licensed by Onyx Pharmaceuticals and is in phase 1 clinical studies. It is a novel antifolate drug resembling TS inhibitors plevitrexed and raltitrexed that combines enzymatic inhibition of thymidylate synthase with α-folate receptor-mediated targeting of tumor cells. Thus, it has potential for efficacy with lower toxicity due to selective intracellular accumulation through α-folate receptor (α-FR) transport. The α-FR, a cell-surface receptor glycoprotein, which is overexpressed mainly in ovarian and lung cancer tumors, has an affinity for 1 similar to that for its natural ligand, folic acid. This study describes a novel synthesis of 1, an X-ray crystal structure of its complex with Escherichia coli TS and 2'-deoxyuridine-5'-monophosphate, and a model for a similar complex with human TS.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
