18668-00-3Relevant articles and documents
Vancomycin binding to low-affinity ligands: Delineating a minimum set of interactions necessary for high-affinity binding
Loll, Patrick J.,Kaplan, Jeffrey,Selinsky, Barry S.,Axelsen, Paul H.
, p. 4714 - 4719 (1999)
Bacterial resistance to vancomycin has been attributed to the loss of an intermolecular hydrogen bond between vancomycin and its peptidoglycan target when cell wall biosynthesis proceeds via depsipeptide intermediates rather than the usual polypeptide int
An efficient synthesis of dichotomine a via cyclization of l-tryptophan derivative
Shi, Xiu Xiao,He, Dian,Li, Shao Bai,Lei, Xin,Yang, Huan
, p. 6387 - 6390 (2013)
A new synthetic method for dichotomine A is reported. The key step of the synthetic process is the efficient cyclization of L-tryptophan derivative via a modified Bischler-Napieralski reaction which aluminium chloride is used as a mild catalyst. Dichotomine A is obtained in 5 steps and 63.9 % yield.
Stereoisomeric lactoyl β methylcholine iodides. Interaction with cholinesterase and acetylcholinesterase
Chan,Robinson
, p. 1057 - 1060 (1974)
The preparation and absolute configuration of the stereoisomeric forms of lactoyl β methylcholine iodide with the 2 racemic forms of the molecule are reported. None of the stereoisomers were substrates for the enzyme acetylcholinesterase, whereas two stereoisomers (L lactoyl β methylcholine and D lactoyl L β methylcholine iodide) were poor substrates for cholinesterase. Results are analyzed in the light of previous studies of the chiral requirements of these 2 enzymes and an attempt is made to define the rate limiting or prohibited step in the enzyme catalyzed reaction with these compounds.
Synthesis, pharmacological evaluation and molecular docking of novel R-/S-2-(2-hydroxypropanamido)-5-trifluoromethyl benzoic acid as dual anti-inflammatory anti-platelet aggregation agents
Rong, Rong,Zhang, Rui-zhen,Wang, Xin,Dan, Yu-han,Zhao, Yun-li,Yu, Zhi-guo
, p. 967 - 978 (2020)
R-/S-2-(2-hydroxypropanamido) benzoic acid (R-/S-HPABA), marine-derived anti-inflammatory antiplatelet drugs, were initially synthesised in our group. However, preliminary research showed that R-/S-HPABA were eliminated rapidly because of extensive hydroxylation metabolism of phenyl ring in vivo. In order to reduce significant hydroxylation metabolism to improve pharmacological activity and bioavailability, trifluoromethyl group was incorporated into R-/S-HPABA to synthesise R-/S-2-(2-hydroxypropanamido)-5-trifluoromethyl benzoic acid (R-/S-HFBA), respectively. The purposes of this study were to report the synthesis of R-/S-HFBA and compare the anti-inflammatory antiplatelet effect and pharmacokinetic properties of R-/S-HFBA with those of R-/S-HPABA. Carrageenan-induced rat paw edema assay was used for the evaluation of the anti-inflammatory activity. R-/S-HFBA showed better results in inhibiting edema and were able to prolong the anti-inflammatory effect after carrageenan injection. The antiplatelet aggregation activity of R-/S-HFBA and R-/S-HPABA was studied on arachidonic acid-induced platelet aggregation of rabbit platelet-rich plasma. The aggregation inhibition rate of R-/S-HFBA was significantly (p max, larger AUC0-∞, and longer t1/2, which, as expected, are more metabolically stable.
A simple procedure for the synthesis of enantiopure α-acetoxy ketones
Babudri, Francesco,Fiandanese, Vito,Marchese, Giuseppe,Punzi, Angela
, p. 2431 - 2440 (1999)
Cross-coupling reactions of α-acetoxy carboxylic acid chlorides with organocopper reagents, derived from Grignard reagents, cuprous bromide and lithium bromide, provide a simple and straightforward method for the synthesis of enantiopure α-acetoxy ketones.
NOVEL STING AGONISTS
-
Paragraph 0756; 0761; 0763, (2020/05/14)
The present invention provides compounds of Formula I′: wherein , W, X, Y, Z, Z1, Z2, R1, R2, R3, R4 and R5 are as defined herein, or a stereoisomer, tautomer, pharmaceutically acceptable salt, prodrug ester or solvate form thereof, wherein all of the variables are as defined herein. These compounds are effective at modulating the STING protein and thus can be used as medicaments for treating or preventing disorders affected by the agonism of STING.
Total Synthesis of (+)-Prunustatin A: Utility of Organotrifluoroborate-Mediated Prenylation and Shiina MNBA Esterification and Macrolactonization to Avoid a Competing Thorpe-Ingold Effect Accelerated Transesterification
Chojnacka, Maja W.,Batey, Robert A.
supporting information, p. 5671 - 5675 (2018/09/13)
A convergent total synthesis of (+)-prunustatin A is described through the assembly of two key fragments and a macrolactonization. Shiina MNBA couplings were used for the formation of each of the four ester bonds in the tetralactone ring, including the key macrocyclization which was essential to minimize competing Thorpe-Ingold accelerated transesterification. Other key steps included an organoboron-based prenylation using potassium prenyltrifluoroborate and a carbonyldiimidazole-mediated coupling to form the salicylamide.
Modifying oligoalanine conformation by replacement of amide to ester linkage
Hongen, Takahiro,Taniguchi, Tohru,Monde, Kenji
supporting information, p. 396 - 401 (2018/02/13)
Oligo(lactic acid) is an ester-analogue of short oligoalanine sequence and adopts a rigid left-handed helical structure. In this study, oligo(lactic acid) was incorporated into oligoalanine sequences and their conformations were studied by vibrational circular dichroism and electronic circular dichroism spectroscopy. The results suggested that oligo(lactic acid) moiety in these sequences maintains a left-handed helix and increases the conformational propensity of the oligoalanine moiety to form a left-handed polyproline type II-like helix. The importance of the chirality of oligo(lactic acid) moiety for the oligoalanine conformation was also studied. The results obtained in this study should be useful in developing ester-containing oligopeptides that function better than normal peptides.
Preparation method and application of 2-lactoyl aminobenzoic acid
-
Paragraph 0037; 0038, (2017/08/30)
The invention relates to a new medicinal application of a chiral compound. The chiral compound is chemically named as R-/S-2-lactoyl aminobenzoic acid and has a structural formula as follows: formula (shown in the description). The compound is initially extracted and separated from secondary metabolite of microorganisms and can be obtained by virtue of a chemical synthetic method. An initial pharmacology experiment shows that the compound has good pain-easing and anti-inflammation activities and relatively low stimulation to gastrointestinal tracts. Recent researches prove that the compound has relatively good anti-platelet aggregation and anti-thrombus activities and is expected to be a novel non-steroidal anti-platelet aggregation and anti-thrombus drug.
Compounds And Compositions for the Treatment of Ocular Disorders
-
Paragraph 0503, (2017/04/11)
The disclosure describes prodrugs and derivatives of prostaglandins, carbonic anhydrase inhibitors, kinase inhibitors, beta-adrenergic receptor antagonists and other drugs, as well as controlled delivery formulations containing such prodrugs and derivatives, for the treatment of ocular disorders.
