83173-71-1

Upstream product

• 74-96-4 ethyl bromide 
• 13574-13-5 Boc-Glu(OBzl)-OH 
• 64-17-5 ethanol 
• 144978-35-8 (S)-ethyl N-tert-butoxycarbonylpyroglutamate 
• 100-51-6 benzyl alcohol 

Downstream Products

• 86938-17-2 2-(S)-tert-butoxycarbonylaminopentanedioic acid 1-ethyl ester 
• 1336933-77-7 C₁₈H₂₅ClN₂O₉S 
• 1336933-34-6 3-[(4S)-4-amino-5-ethoxy-5-oxopentanamido]-5-chloro-2-hydroxybenzene-1-sulfonic acid 

Relevant academic research and scientific papers

Synthesis of diacylated γ3-glutamyl-cysteamine prodrugs, and in vitro evaluation of their cytotoxicity and intracellular delivery of cysteamine

To overcome the major disadvantages of cysteamine, the only registered treatment for the rare genetic disease cystinosis, nine prodrugs of γ3-glutamyl-cysteamine (4) were synthesized for evaluation. Esterification of the thiol conferred oxidative stabilit

Regioselective Ring Opening of Chiral N-Boc Protected Pyroglutamate and Pyroaminoadipate Ethyl Esters with Heteronucleophiles

Mixed diesters, ω-amide and ω-thioesters are obtained from both N-Boc ethyl pyroglutamate and pyroaminoadipate under neutral or basic conditions.Under neutral conditions, the reaction is catalyzed by KCN and the use of ultrasound speeds up the process.In

PRODUCTION PROCESSES OF S- AND O-DIACYLATED GAMMA-GLUTAMYL-CYSTEAMINE PRODRUGS

Methods are provided for the synthesis of a compound of formula (X). R2 is selected from -H, -C1-C4-alkyl,-C2-C4-alkenyl and C1-C4-aryl; R3 is selected from -C(O)H and

A pemetrexed quality control method and pemetrexed impurity and its salt preparation

The invention provides a pemetrexed quality control method, and preparation of a pemetrexed impurity and salt thereof. The pemetrexed impurity is synthesized from the raw material N-tert-butoxycarbonyl-L-glutamic acid-5-benzyl ester. The pemetrexed qualit

PROPHYLACTIC AGENT OR THERAPEUTIC AGENT FOR DIABETES OR OBESITY

A medicament having an excellent CaSR agonist action which enables the prevention or treatment of diabetes or obesity is provided by a composition comprising the compound represented by general formula (I) as defined, or a salt thereof.

PYRIDINE DERIVATIVES SUBSTITUTED WITH HETEROCYCLIC RING AND gamma-GLUTAMYLAMINO GROUP, AND ANTIFUNGAL AGENTS CONTAINING SAME

The present invention provides an antifungal agent which has excellent antifungal action, and which is also excellent in terms of its properties, and in particular its solubility in water and safety. The present invention discloses a compound represented

Reversal of multiple drug resistance in cholangiocarcinoma by the glutathione S-transferase-π-specific inhibitor O 1-hexadecyl-γ-glutamyl-S-benzylcysteinyl-D-phenylglycine ethylester

Cholangiocarcinoma is markedly resistant to chemotherapy and has a dismal prognosis, but its mechanism of drug resistance is unknown. This study examines whether glutathione S-transferase-π (GSTP1-1) is involved in resistance to anticancer drugs in cholangiocarcinoma and whether GSTP1-1-specific inhibitors can overcome this resistance. First, immunohistochemical examination disclosed strong staining of all our 17 cholangiocarcinoma specimens for GSTP1-1, irrespective of histological type. Transfection of the GSTP1-1 antisense expression vector into a human cholangiocarcinoma cell line (HuCCT1) apparently decreased its intracellular GSTP1-1 concentration, and the sensitivity of transfectants to adriamycin (ADR), cisplatin, and alkylating agents such as melphalan and 4-hydroxyperoxycyclophosphamide (4-HC) was increased significantly, compared with that of mock transfectants. We next synthesized GSTP1-1-specific inhibitors by elongating the carbon chain of the ethylester at the N-terminal of γ-glutamyl-S-benzylcysteinyl-phenylglycyl diethylester and performed a pharmacokinetic study on them. Of six GSTP1-1 inhibitors tested, O1-hexadecyl-γ-glutamyl-S-benzylcysteinyl-D-phenylglycine ethylester (C16C2) showed the smallest volume of central compartment and smallest volume of distribution at steady state and the second smallest clearance, being the most effective inhibitor in vivo. The IC50 value of ADR or 4-HC for HuCCT1 cells decreased greater by treatment with C16C2 in a dose-dependent manner, paralleling the decrease in GSTP1-1 activity, than that of ADR or 4-HC alone. The antitumor activity of ADR or cyclophosphamide was clearly enhanced by combination therapy with C16C2 in a xenograft model. In conclusion, our results demonstrated that GSTP1-1 is a resistance factor for anticancer drugs in cholangiocarcinoma and that C16C2, a GSTP1-1-specific inhibitor, is a potent agent against the resistance.

Fatty acid analogs and prodrugs

Novel derivatives of fatty acid analogs that have from one to three heteroatoms in the fatty acid moiety which can be oxygen, sulfur or nitrogen, are disclosed in which the carboxy-terminus has been modified to form various amides, esters, ketones, alcohols, alcohol esters and nitrites thereof. These compounds are useful as substrates for N-myristoyltransferase (NMT) and/or its acyl coenzyme, and as anti-viral and anti-fungal agents or pro-drugs of such agents. Illustrative of the disclosed compounds are fatty acid amino acid analogs of the structure STR1 in which x is the ethyl or t-butyl ester of an amino acid such as Gly, L-Ala, L-Ile, L-Phe, L-Trp, L-Thr or an amide such as NHCH2 C6 H5 or NH(CH2)2 C6 H5.

Papain-catalyzed esterification of N(α)-protected amino acids and dipeptides with ethanol in different organic systems

The papain-catalyzed esterification of N(α)-protected amino acids and dipeptides with ethanol in mostly hydrophobic organic solvent systems containing low amounts of water has been investigated. The influence of various parameters, such as the amount of added water, reaction time, temperature and pH of added buffer, on the yield of ester was studied first on the model substrate Z-Ala. The optimized reaction conditions were then used for esterification of a series of N(α)-protected amino acids and dipeptides.

Fatty acid analogs and prodrugs

Novel derivatives of fatty acid analogs that have from one to three heteroatoms in the fatty acid moiety which can be oxygen, sulfur or nitrogen, are disclosed in which the carboxy-terminus has been modified to form various amides, esters, ketones, alcohols, alcohol esters and nitriles thereof. These compounds are useful as substrates for N-myristoyltransferase (NMT) and/or its acyl coenzyme, and as anti-viral and anti-fungal agents or pro-drugs of such agents. Illustrative of the disclosed compounds are fatty acid amino acid analogs of the structure STR1 in which X is the ethyl or t-butyl ester of an amino acid such as Gly, L--Ala, L--Ile, L--Phe, L--Trp, L--Thr or an amide such as NHCH2 C6 H5 or NH(CH2)2 C6 H5,