33912-87-7Relevant articles and documents
Rational Design of Small Peptides for Optimal Inhibition of Cyclooxygenase-2: Development of a Highly Effective Anti-Inflammatory Agent
Singh, Palwinder,Kaur, Sukhmeet,Kaur, Jagroop,Singh, Gurjit,Bhatti, Rajbir
supporting information, p. 3920 - 3934 (2016/05/24)
Among the small peptides 2-31, (H)Gly-Gly-Phe-Leu(OMe) (30) reduced prostaglandin production of COX-2 with an IC50 of 60 nM relative to 6000 nM for COX-1. The 5 mg kg-1 dose of compound 30 rescued albino mice by 80% from capsaicin-induced paw licking and recovered it by 60% from carrageenan-induced inflammation. The mode of action of compound 30 for targeting COX-2, iNOS, and VGSC was investigated by using substance P, l-arginine, and veratrine, respectively, as biomarkers. The interactions of 30 with COX-2 were supported by isothermal calorimetry experiments showing a Ka of 6.10 ± 1.10 × 104 M-1 and ΔG of -100.3 kJ mol-1 in comparison to a Ka 0.41 × 103 ± 0.09 M-1 and ΔG of -19.2 ± 0.06 kJ mol-1 for COX-1. Moreover, compound 30 did not show toxicity up to a 2000 mg kg-1 dose. Hence, we suggest peptide 30 as a highly potent and promising candidate for further development into an anti-inflammatory drug.
Total syntheses of arenamides A, B and C
Chandrasekhar, Srivari,Sathish, Kurapati,Reddy, Gangireddy Pavan Kumar,Mainkar, Prathama S.
, p. 348 - 355 (2014/04/03)
Total syntheses of the three arenamides A-C, NFκB inhibitors, are described for the first time. The key steps involved in the synthesis are a Crimmin's aldol, Wittig olefination and a macrolactamization reaction.
Total synthesis of arenamide A and its diastereomer
Chandrasekhar,Pavankumarreddy,Sathish
scheme or table, p. 6851 - 6854 (2010/05/03)
Arenamide A and its diastereomer have been synthesized in a convergent fashion. The key steps involved in this synthesis are Sharpless asymmetric epoxidation, C-C bond formation, and macrolactamization.
An Effective Water-Free Aprotic System for Dissolving Free Amino Acids
Raydnov, M. G.,Klimenko, L. V.,Mitin, Yu. V.
, p. 283 - 287 (2007/10/03)
An effective water-free system was proposed for dissolution and subsequent use in peptide synthesis of free amino acids and their derivatives. It consists of dimethylformamide, a tertiary base, and inorganic additives. Neutral salts (CF3COONa, Ba(ClO4)2, Ca(ClO4)2, NaClO4, BaI2, or Ca(NO3)2) serve as the inorganic additives that increase the solubility of free amino acids in dimethylformamide and provide true 0.2-3 M amino acid solutions. Triethylamine and N-methylmorpholine are most suitable as the tertiary bases. This system was used in reactions with acylating agents: Boc2O, ZOSu, FmocOSu, and activated derivatives of Nα-protected amino acids or peptides. The corresponding amino acid derivatives or Nα-protected di-, tri-, and tetrapeptides were obtained in yields of 80-99 percent at the reaction times of 30-240 min.
Use of polymer-bound 4-dialkylaminopyridines in peptide synthesis
Frontin, F. Cavelier,Guendouz, F.,Jacquier, R.,Verducci, J.
, p. 463 - 467 (2007/10/02)
This work describes the use of polymer-bound 4-dialkylaminopyridines as catalyst in peptide bond formation.In comparison with their soluble analogues, such as DMAP, these less basic compounds are less favorable to formation of oxazolone intermediate, and lead to peptide bond formation in good yields, and generally very low racemization. Key words: DMAP; polymer-bound dialkylaminopyridines; peptide synthesis; racemization.
