3373-59-9Relevant academic research and scientific papers
Clickable glycopeptoids for synthesis of glycopeptide mimic
Singhamahapatra, Anadi,Sahoo, Laxminarayan,Loganathan, Duraikkannu
, p. 10329 - 10336 (2013)
Structurally diverse novel glycopeptoids were synthesized which can be attached to biologically important peptides by click reaction to improve their potential to be used in medicinal chemistry. Triazole-linked αβ-hydrid glycopeptoids were synthesized that mimic the conserved linkage region of N-linked glycoproteins in eukaryotes. The amide bonds were replaced with triazole rings, and αβ-hybrid peptoids were introduced as the backbone modification in peptidomimetics. In addition to their facile synthesis, these modifications have the possibility of introducing otherwise impossible conformations in the peptide backbone.
Synthesis and Conformational Analysis of Aminopyrazolonyl Amino Acid (APA)/Peptides
Bollu, Amarnath,Sharma, Nagendra K.
, p. 1286 - 1292 (2019)
Pyrazole, pyrazolone, and aminopyrazolone derived molecules are bioactive molecules and considered as potential therapeutic drug candidates because of their unique structural properties. These molecules have abilities to interact with several bio-macromolecules via non-covalent interactions such as hydrogen bonding and π–π interactions. In structural organization of dipeptides, pyrazole containing aromatic amino acid/dipeptides have been explored and considered as potential amino acid residue. In repertoire of unnatural aromatic amino acids, this report describes the synthesis of 4-aminopyrazolonyl containing amino acids and their crystal structures. The incorporation of 4-aminopyrazolonyl at N-terminal of native amino acid/dipeptides influences the conformational changes of respective peptide which induces the formation of distinctive supramolecular self-assembly structures such as β-sheet and α-helices in their solid-state crystal. The structural conformation of those peptides, here, are also demonstrated in solution phase by 1H-NMR (1D/2D) and [D6]DMSO titration methods which support the formation of inter-/intramolecular hydrogen bonding in solution. Hence, these unnatural amino acid analogues can tune the secondary structure of natural amino acid/peptides by introducing at N-terminal via amide bond.
Synthesis of Ethyl cis-2--7-oxo-3-phenyl-6-phthalimido-1-azabicyclohept-3-ene-2-carboxylate and Methyl cis-2-Bromo-3-methyl-8-oxo-7-phthalimido-4-oxa-1-azabicyclooctane-2-carboxylate
Hakimelahi, Gholam H.,Jarrahpour, Ali A.
, p. 1501 - 1505 (1989)
Th synthesis of Δ1-carbapenem and two β-lactams possessing a Br-atom at the N-substituting center not involved in the lactam ring and bearing the carboxyl group is described.The β-lactams having this kind of Br-substitution are more susceptible to nucleophilic attack than those having a conjugated double bond with the N-atom of the β-lactam ring.DBU is found to be an excellent reagent for the elimination of the silyloxy function.Moreover, a simple method for the addition of diethyl phosphite to an α,β-unsaturated double bond using a catalytic amount of NaH is described.
NOVEL TRITERPENE DERIVATIVES AS HIV INHIBITORS
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Page/Page column 51, (2021/08/20)
The present invention relates to novel triterpene derivatives of formula (I); and pharmaceutically acceptable salts thereof, wherein R1, R2, R3, R4, n, and ring (II) are as defined in formula (I). The invention also relates to novel triterpene derivatives, related compounds, and pharmaceutical compositions useful for the therapeutic treatment of viral diseases and particularly HIV mediated diseases.
Visible-Light Mediated Tryptophan Modification in Oligopeptides Employing Acylsilanes
Reimler, Jannik,Studer, Armido
supporting information, p. 15392 - 15395 (2021/10/04)
A method for the selective tryptophan modification and labelling of tryptophan-containing peptides is described. Photoirradiation of acylsilanes generates reactive siloxycarbenes which undergo H?N-insertion into the indole moiety of tryptophan to give stable silyl protected hemiaminals. This method is successfully applied to chemically modify various tryptophan containing oligopeptides. The method enables the selective introduction of alkynes to peptides that are eligible for further alkyne-azide click chemistry. In addition, the dansyl fluorophore can be conjugated to a peptide using this approach.
Synthesis method of aztreonam main ring synthesis intermediate N-carbobenzoxy-L-threonine amide
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Paragraph 0018-0024, (2020/05/01)
The invention provides a synthesis method of aztreonam main ring synthesis intermediate N-carbobenzoxy-L-threonine amide, which comprises the following steps: 1) adding an L-threonine solid and methanol into a reaction kettle, stirring, cooling, dropwisely adding thionyl chloride, carrying out heating reflux reaction, and drying a solvent by distillation; (2) adding methanol into a reactant obtained in the step (1) for dissolving, heating and pressurizing, introducing liquid ammonia, keeping the temperature and the pressure, evaporating the liquid ammonia after the reaction is finished, and evaporating the solvent to dryness; and 3) adding water into a reaction product obtained in the step 2) for dissolving, dropwise adding benzyl chloroformate, dropwise adding an acid-binding agent solution to control the pH value of the reaction system to obtain intermediate N-carbobenzoxy-L-threonine amide, and carrying out filter pressing and drying to obtain a solid.
NOVEL TRITERPENE DERIVATIVES AS HIV INHIBITORS
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Page/Page column 34, (2020/08/28)
The present invention relates to novel triterpene derivatives of formula (I); and pharmaceutically acceptable salts thereof, wherein R1, R2, R3, R4, and ring are as defined herein. The invention also relates to novel triterpene derivatives, related compounds, and pharmaceutical compositions useful for the therapeutic treatment of viral diseases and particularly HIV mediated diseases.
PROCESS AND INTERMEDIATES FOR SYNTHESIS OF PEPTIDE COMPOUNDS
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Paragraph 0170, (2019/02/13)
Disclosed is a new process and intermediates for preparing dipyrrolidine peptide compounds such as, for example, rapastinel. Advantageously, the process may be industrially scalable and cost-effective and use less toxic reagents and/or solvents. Further, the process may be used to prepare peptide compounds having improved purity.
Synthesis method of aztreonam monocyclic mother nucleus
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Paragraph 0046; 0047, (2019/06/13)
The invention discloses a synthesis method of an aztreonam monocyclic mother nucleus, and mainly relates to the technical field of pharmaceutical and chemical industry. The method comprises the stepsthat L-threonine is subjected to methyl esterification; terbutyloxycarbonyl anhydride is used for performing amino BOC protection; ammonia water is subjected to ammonolysis; under the catalysis of a solid basic catalyst, methyl-sulfuric-acyl reaction and sulfonation are performed; cyclization, deprotection and acidification are performed to obtain the aztreonam monocyclic mother nucleus. The raw materials are cheap and can be easily obtained; the yield is high; the cost is low; the synthesis method belongs to a green, energy-saving and environment-friendly practical technology.
Synthesis and evaluation of in vivo anti-hypothermic effect of all stereoisomers of the thyrotropin-releasing hormone mimetic: Rovatirelin Hydrate
Kobayashi, Naotake,Sato, Norihito,Sugita, Katsuji,Takahashi, Kouji,Sugawara, Tamio,Tada, Yukio,Yoshikawa, Takayoshi
, (2019/11/20)
We discovered the orally active thyrotropin-releasing hormone (TRH) mimetic: (4S,5S)-5-methyl-N-{(2S)-1-[(2R)-2-methylpyrrolidin-1-yl]-1-oxo-3-(1,3-thiazol-4-yl)propan-2-yl}-2-oxo-1,3-oxazolidine-4-carboxamide 1 (rovatirelin). The central nervous system (CNS) effect of rovatirelin after intravenous (iv) administration is 100-fold higher than that of TRH. As 1 has four asymmetric carbons in its molecule, there are 16 stereoisomers. We synthesized and evaluated the anti-hypothermic effect of all stereoisomers of 1, which has the (4S),(5S),(2S),(2R) configuration from the N-terminus to the C-terminus, in order to clarify the structure?activity relationship (SAR) of stereoisomers. The (4R),(5R),(2R),(2S)-isomer 16 did not show any anti-hypothermic effect. Only the (4S),(5S),(2S),(2S)-isomer 10, which has the (2S)-2-methylpyrrolidine moiety at the C-terminus showed the anti-hypothermic effect similar to 1. Stereoisomers, which have the (5R) configuration of the oxazolidinone at the N-terminus and the (2R) configuration at the middle-part, showed a much lower anti-hypothermic effect than that of 1. On the other hand, stereoisomers, which have the (4R) configuration of the oxazolidinone at the N-terminus or the (2S) configuration of the C-terminus, have little influence on the anti-hypothermic effect.
