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1.
Substituted cyclodextrins (CDs) have many applications, but synthetic challenges have limited the derivatives that can routinely be accessed. In particular, although there is considerable interest in selective derivatization at the 2- and 3-hydroxyls on the secondary face, since bulky guest molecules are most likely to project through this larger aperture, syntheses of such derivatives have required arduous procedures that afford poor yields, limiting their accessibility and utility. We address this challenge via synthetic strategies that allow facile creation of diverse libraries of water-soluble mono-3-substituted-β-cyclodextrins, via the commercially available mono-3-amino-β-cyclodextrin. The power of these strategies is confirmed through synthesis of twenty water-soluble cyclodextrin analogues with amide, thioureas or urea linkers, using one-pot reactions producing ≥55% yields and purifications that do not require chromatography. This work opens new possibilities for the design of selective host molecules for use in supramolecular chemistry, chemical separations, pharmaceutical formulations, and calibration of molecular simulations. 相似文献
2.
Barbier J Wegner J Benson S Gentzsch J Pietschmann T Kirschning A 《Chemistry (Weinheim an der Bergstrasse, Germany)》2012,18(29):9083-9090
The total synthesis of 16 new ion channel inhibitors derived from noricumazole?A, a secondary metabolite from the myxobacterium Sorangium cellulosum, is reported. Particular focus of library design is put on stereochemical permutations in the central region (C9 and C11), the oxazole moiety and the side chain at C4 of the isochromanone moiety. Noricumazole?A and all new noricumazole derivatives were tested in an assay system with inhibitory effect on the hepatitis?C virus (HCV) life cycle. Most of them are moderate to strong HCV inhibitors (350?nM-6?nM) but also exert pronounced cytotoxicity. In contrast, the thiazole analogue of noricumazole?A is a strong HCV inhibitor with only moderate cytotoxic property. It may become a lead structure with a good therapeutic index (CC(50)/IC(50)) of greater than 10. 相似文献
3.
Kai Zhang Huai-Wei Ding Hao Ju Qi Huang Li-Juan Zhang Hong-Rui Song De-Cai Fu 《中国化学快报》2015,26(6):801-803
A series of sulfenimine cephalosporin sulfoxide derivatives(7a–v) were designed, synthesized and evaluated for their inhibitory activity against TEM-1 and cephalosporinase in cell-free systems. Some of the tested compounds showed enhanced inhibitory activity against class C b-lactamase cephalosporinase compared with the tazobactam. The most promising compounds 7c and 7n(IC50= 7.6 and8.6 mmol/L, respectively) were further investigated in combination with cefradine against a variety of clinical isolated b-lactamase-producing bacterial strains. 相似文献
4.
N. G. Morozova Yu. G. Sachkova G. A. Serebrennikova L. V. Volkova R. P. Evstigneeva 《Chemistry of Natural Compounds》1991,27(1):12-14
The stereoselective synthesis of a -D-phosphatidylgalactose has been achieved by the interaction of a benzyl phosphatidate with D-galactose tert-butyl orthoacetate or trichloroacetimidate.M. V. Lomonosov Institute of Fine Chemical Technology, Moscow. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 16–19, January–February, 1991. 相似文献
5.
Rhodium catalyzed O-H insertion reactions employing α-diazophosphonate 20 with appropriately protected thymidine, uridine, cytosine, adenosine and guanosine derivatives leads to novel 5'-phosphononucleoside derivatives. Deprotection led to a novel series of phosphono derivatives bearing a carboxylic acid moiety adjacent to the phosphonate group with potential antiviral and/or anticancer activity. The phosphononucleosides bearing an α-carboxylic acid group are envisaged as potential diphosphate mimics. Conversion to mono- and diphosphorylated phosphononucleosides has been effected for evaluation as nucleoside triphosphate mimics. Most of the novel phosphononucleosides proved to be inactive against a variety of DNA and RNA viruses. Only the phosphono AZT derivatives 56-59 showed weak activity against HIV-1 and HIV-2. 相似文献
6.
Qing Jie Zhao Yan Song Hong Gang Hu Shi Chong Yu Qiu Ye Wu School of Pharmary Second Military Medical University Shanghai China 《中国化学快报》2007,18(6):670-672
Twenty-three 1 -(1H-1,2,4-triazole-1 -y1)-2-(2,4-difluorophenyl)-3-(iV-cycloproyl-N-substituted-amino)-2-propanols were designed and synthesized on the basis of the active site of lanosterol 14α-demethylase. In vitro antifungal activities showed that some of the title compounds had higher antifungal activity and broader antifungal spectrum than fluconazole. 相似文献
7.
《Tetrahedron letters》2019,60(22):1471-1475
The total synthesis of four natural products, trigonostemine A, trigonostemine B, pityriacitrin, and hyrtiosulawesine was accomplished. The key intermediates, variously substituted 1-formyl-β-carbolines, were prepared in five steps via a novel synthetic approach using readily available starting materials. These formyl derivatives were then further transformed, providing a general route for the synthesis of the four title alkaloids. The method reported herein represents the first total synthesis of the two trigonostemines and a new pathway to pityriacitrin and hyrtiosulawesine. 相似文献
8.
Jun Feng Ying Lu Zhe Feng Cai Shi Peng Zhang Zong Ru Guo 《中国化学快报》2007,18(1):45-47
A series of thiazolidinediones analogs,as PPAR modulators,were designed,synthesized and evaluated in vitro. 相似文献
9.
Design and efficient synthesis of novel haptens and complete antigens for the AOZ, a toxic metabolite of furazolidone 总被引:1,自引:0,他引:1
Yu Dong Shen Yu Wang Shi Wei Zhang Zhi LiXiao Yuan Ming Sun Xian Zhang Bu Lian Quan Gu 《中国化学快报》2007,18(12):1490-1492
A good strategy was brought forward for designing efficient haptens and complete antigens for 3-amino-2-oxazolidinone (AOZ). Haptens designed newly were achieved facilely in good yield by using LiCI-N(Et)_3 as new catalysis system,the structure of which was elucidated by spectroscopy analysis,such as NMR and MS.Novel antigens for AOZ were prepared successfully by convenient active ester method.The ratios of haptens 3 and 4 to carrier proteins were proven respectively as 41:1(5a),39:1(6a),11:1(5b) and 9:1(6b) by trinitrobenzene sulfonic acid(TNBS) method.The results of indirect competitive ELISA (ic-ELISA) of antiserums indicated that the haptens with a short unsaturated side chain can evoke specific immune response effectively. 相似文献
10.
Tarbe M Azcune I Balentová E Miles JJ Edwards EE Miles KM Do P Baker BM Sewell AK Aizpurua JM Douat-Casassus C Quideau S 《Organic & biomolecular chemistry》2010,8(23):5345-5353
β-Lactam peptides were envisioned as conformational constraints in antigenic peptides (APs). Three different β-lactam tripeptides of varying flexibility were prepared in solution and incorporated in place of the central part of the altered melanoma associated antigenic peptide Leu(27)-Melan-A(26-35) using solid phase synthesis techniques. Upon TFA cleavage from the solid support, an unexpected opening of the β-lactam ring occurred with conservation of the amide bond. After adaptation of the solid phase synthesis strategy, β-lactam peptides were successfully obtained and both opened and closed forms were evaluated for their capacity to bind to the antigen-presenting class-I MHC HLA-A2 protein system. None of the closed β-lactam peptides bound to HLA-A2, but their opened variants were shown to be moderate to good HLA-A2 ligands, one of them being even capable of stimulating a Melan-A-specific T cell line. 相似文献
11.
Xiao-Qian Chi Bo Hou Liu Yang Cheng-Ting Zi Yong-Feng Lv Jin-Yu Li 《Natural product research》2020,34(10):1380-1388
Abstractα-mangostin, a polyphenol xanthone derivative, was mainly isolated from pericarps of the mangosteen fruit (Garcinia mangostana L.). In present investigation, a series of derivatives were designed, synthesised and evaluated in vitro for their inhibitory activity of acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE). Among the synthesised xanthones, compounds 1, 9, 13 and 16 showed AChE selective inhibitory activity, 15 was a BuChE selective inhibitor while 2, 3, 5, 6, 7, 12 and 14 were dual inhibitors. The most potent inhibitor of AChE was 16 while 5 was the most potent inhibitor of BuChE with IC50 values of 5.26?μM and 7.55?μM respectively. 相似文献
12.
Jing Yang Xiaofang Wang Hui Wen Fang Qin Guang Zhong Yang 《中国化学快报》2007,18(7):814-816
A series of phenylbenzamidine analogs were synthesized and tested for their biological activities of inhibiting the reuptake of 5- HT. All of them were new compounds, and their structures were confirmed by 1HNMR, MS and XRD. 相似文献
13.
Qiu Qin He Ke Li Yong Bing Cao Huan Wen Dong Li Hua Zhao Chao Mei Liu Chun Quan Sheng School of Pharmacy Second Military Medical University Shanghai China 《中国化学快报》2007,18(6):663-666
Based on the active site of Candida albicans lanosterol 14α-demethylase (CACYP51), novel triazole compounds structurally different from the current triazole drugs were designed and synthesized. In vitro antifungal activities showed that compounds 10,11, 16 and 20 exhibited strong activities. In addition, compounds 10,11 and 16 also displayed certain activities against fluconazole-resistant fungi. 相似文献
14.
MK-7655 (1) is a β-lactamase inhibitor in clinical trials as a combination therapy for the treatment of bacterial infection resistant to β-lactam antibiotics. Its unusual structural challenges have inspired a rapid synthesis featuring an iridium-catalyzed N-H insertion and a series of late stage transformations designed around the reactivity of the labile bicyclo[3.2.1]urea at the core of the target. 相似文献
15.
A short and efficient synthesis for β-acyl and β-alkoxycarbonyl heterocyclic sulfones containing benzothiazol (BT) and phenyltetrazol (PT) heterocyclic core is presented here. The method seems to be general and provides the desired C-nucleophiles in very good to excellent yields from readily available starting materials. 相似文献
16.
Khalid M. Khan Nida Ambreen Muhammad Taha Sobia A. Halim Zaheer-ul-Haq Shagufta Naureen Saima Rasheed Shahnaz Perveen Sajjad Ali Mohammad Iqbal Choudhary 《Journal of computer-aided molecular design》2014,28(5):577-585
Using structure-based virtual screening approach, a coumarin derivative (1) was identified as β-glucuronidase inhibitor. A focused library of coumarin derivatives was synthesized by eco-benign version of chemical reaction, and all synthetic compounds were characterized by using spectroscopy. These compounds were found to be inhibitor of β-glucuronidase with IC50 values in a micromolar range. All synthetic compounds exhibited interesting inhibitory activity against β-glucuronidase, however, their potency varied substantially from IC50 = 9.9–352.6 µM. Of twenty-one compounds, four exhibited a better inhibitory profile than the initial hit 1. Interestingly, compounds 1e, 1k, 1n and 1p exhibited more potency than the standard inhibitor with IC50 values 34.2, 21.4, 11.7, and 9.9 µM, respectively. We further studied their dose responses and also checked our results by using detergent Triton ×-100. We found that our results are true and not affected by detergent. 相似文献
17.
A straightforward, highly stereoselective protocol toward the synthesis of deuterium-labeled (2R,3S,4S)-β-cyclohexenylserine has been developed. Key steps are a Nozaki-Hiyama-Kishi reaction generating the stereogenic centers and a ring-closing metathesis for the construction of the cyclohexenyl ring system. The labeled amino acid was further activated as an SNAc-ester for feeding experiments. 相似文献
18.
The relay stations play a significant role in long-range charge hopping transfer in proteins. Although studies have clarified that many more protein structural motifs can function as relays in charge hopping transfers by acting as intermediate charge carriers, the relaying properties are still poorly understood. In this work, taking a β-turn oligopeptide as an example, we report a dynamic character of a relay with tunable relaying properties using the density functional theory calculations. Our main finding is that a β-turn peptide can serve as an effective electron relay in facilitating long-range electron migration and its relay properties is vibration-tunable. The vibration-induced structural transient distortions remarkably affect the lowest occupied molecular orbital (LUMO) energy, vertical electron affinity and electron-binding mode of the β-turn oligopeptide and the singly occupied molecular orbital (SOMO) energy of the corresponding electron adduct and thus the relaying properties. Different vibration modes lead to different structural distortions and thus have different effects on the relaying properties and ability of the β-turn peptide. For the relaying properties, there approximately is a linear negative correlation of electron affinity with the LUMO energy of the β-turn or the SOMO energy of its electron adduct. Besides, such relaying properties also vary in the vibration evolution process, and the electron-binding modes may be tunable. As an important addition to the known static charge relaying properties occurring in various protein structural motifs, this work reports the dynamic electron-relaying characteristics of a β-turn oligopeptide with variable relaying properties governed by molecular vibrations which can be applied to different proteins in mediating long-range charge transfers. Clearly, this work reveals molecular vibration effects on the electron relaying properties of protein structural motifs and provides new insights into the dynamics of long-range charge transfers in proteins. © 2018 Wiley Periodicals, Inc. 相似文献
19.
The present study reports the synthesis, spectral characterization, self-assembly properties, and preliminary in vitro study of antioxidant capacity of two triple covalent hybrids consisting of fullerene C60, peptide, and steroidal moiety. Previously synthesized fulleropyrrolidinic acid and pregnenolone were connected by peptide linker using a multistep DCC/DMAP and/or EDC/HOBT esterification/amidation procedure. The hybrids were characterized by comparative analysis of spectroscopic data obtained from FTIR, UV–vis, HRMS, and extensive NMR experiments (1H, 13C, COSY, HSQC, and HMBC). The self-assembling properties and morphology of triads samples prepared by drop-drying method were examined by scanning electron microscopy (SEM). Preliminary in vitro antioxidant activity was studied by Ferrous ion Oxidation-Xylenol orange (FOX) method. 相似文献
20.