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1.
[reaction: see text] A 4-methyl-5-oxo docetaxel analogue has been prepared starting from 10-deacetylbaccatin III. This new D-seco docetaxel analogue is slightly less potent than docetaxel at microtubule stabilization in vitro and has about 1/1000th the cytotoxicity of docetaxel. The lack of improved activity for this compound compared to other D-modified taxoids confirms that a C-5 oxygen atom is not required for biological activity. 相似文献
2.
Zhou FS Tang WD Mu Q Yang GX Wang Y Liang GL Lou LG 《Chemical & pharmaceutical bulletin》2005,53(11):1387-1391
Nineteen new derivatives of the naturally occurring compound, goniothalamin, were prepared by chemical modification and semi-synthetic methods. The antitumor activities of these derivatives and goniothalamin were evaluated in vitro against human tumor cell lines, and most of them showed an inhibitory effect against HL-60 cancer cells. The derivatives 10-nitro-goniothalamin and 10-amino-goniothalamin gave selective inhibition concentration (IC50) of 1.10 and 1.14 microg/ml, respectively, against human stomach cancer SGC-7901 cells, while that of etoposide (vp-16) as the positive control was 6.07 microg/ml. Finally, the partition coefficients, logP (pi values), of these derivative molecules, were evaluated by calculating the additive approximate organic fragment logP value. 相似文献
3.
Jean-Pierre Pulicani Daniel Bzard Jean-Dominique Bourzat Herv Bouchard Martine Zucco Dominique Deprez Alain Commeron 《Tetrahedron letters》1994,35(52):9717-9720
A new route to semisynthetic 2-modified docetaxel analogs is described using electrochemical cleavage of the 2-benzoate as the key reaction. Subsequent reacylation at C-2 followed by sequential deprotections afforded the title analogs. Biological results of selected 2-docetaxel analogs are presented. 相似文献
4.
R. Meusinger J. Heinicke K. Möhle M. Mühlstädt 《Monatshefte für Chemie / Chemical Monthly》1996,127(11):1145-1152
Summary Addition of sulfur dichloride to tetrachlorocatechol-bisallylether (1) yields the 9- and 10-ring thia crown ether derivatives2 and3, respectively, together with the dithia-18-crown-6-ether4. The 10-membered ring compound3 represents the first thia macrocycle containing bothMarkovnikov andanti-Markovnikov constitution of the -chloro-thio structural segments in the same molecule. By1H and13C NMR spectroscopy, equal amounts of two preferred conformers of the only isolated diastereomer of3 were observed at temperatures below –50°C. The signals were assigned to these conformers using COSY, HETCOR, and phase sensitive NOESY spectra at low temperatures. The preferred conformations and the relative configuration were determined using the different effects of
gauche
-and
anti
-positions in13C NMR chemical shifts and analyzing vicinal3
J
H,H coupling constants. These results were confirmed by molecular mechanics calculations.Dedicated to Prof. Dr.Rolf Borsdorf on the occasion of his 65th birthday 相似文献
5.
Gonçalves AG Noseda MD Duarte ME Grindley TB 《The Journal of organic chemistry》2007,72(26):9896-9904
Long-chain alkyl ether derivatives of sulfated oligosaccharides were semisynthesized as follows: two naturally occurring red seaweed galactans (neutral agarose and kappa-carrageenan) were submitted to partial reductive hydrolysis to give neutral and sulfated oligosaccharide alditols. The neutral disaccharide alditol (1) and its trityl ether (5) were sulfated and/or alkylated through formation of their dibutylstannylene or (bis)dibutylstannylene acetals. In these reactions, the dibutylstannylene acetals of the terminal 1,2-diols in the alditol units were more reactive than those formed on the cis-diols of the galactopyranosidic units. This property allowed the regioselective monoalkylation of a neutral tetrasaccharide alditol (2), which contained eleven free hydroxyl groups, the highest selectivity ever observed with dibutylstannylene acetals. An alkylated/sulfated derivative (11) was also obtained through the regioselective alkylation of a naturally sulfated disaccharide alditol (10, a kappa-carrageenan derivative). 相似文献
6.
E. V. Rumyantsev E. V. Antina M. B. Berezin 《Russian Journal of Physical Chemistry A, Focus on Chemistry》2006,80(7):1093-1098
This paper presents the IR spectra of solid alkyl substituted α,α-, α,β-, and β,β-dipyrrolylmethene hydrobromides and their oxa and thia derivatives recorded in KBr pellets over the frequency range 400–4000 cm?1. The conclusion was drawn that the NH bonds in the pyrrole fragments of α,α-dipyrrolylmethene were identical, as distinct from the α,β and β,β isomers. The influence of functional substitution in the dipyrrolylmethene molecule on the frequencies of NH stretching vibrations was discussed. A satisfactory correlation between NH bond vibrational frequencies and the enthalpies of vaporization of gaseous hydrogen bromide from crystalline samples under heating was observed. This allows the IR data to be used as a criterion of the stability of dipyrrolylmethene salts and their oxa and thia derivatives. 相似文献
7.
An expedient synthetic route to E-ring extended estrone derivatives is reported. Estrone-derived cyclopentenones were accessed by an intermolecular Pauson-Khand (PK) cycloaddition. It was found that electron donating and withdrawing substituents in the arylalkyne increased and decreased the yields of PK products, respectively. The stereochemistry of the products was elucidated by X-ray and NMR studies. 相似文献
8.
The total synthesis of a trans-position butenolide analogue of triptolide 3 and the semi-synthesis of analogue 4, with a furan ring, and compound 5, without a planar D-ring, are described. Studies into the antitumor activity of these compounds suggest that the five-membered unsaturated lactone ring (D-ring) of triptolide is essential to its potent anticancer activity and the C18 carbonyl group may exert an important influence on the interaction between triptolide and the target molecule(s) responsible for initiating their cytotoxic effects. 相似文献
9.
Gelmi ML Nava D Leone S Pellegrino S Baldelli E Zunino F Cappelletti G Cartelli D Fontana G 《The Journal of organic chemistry》2008,73(22):8893-8900
The synthesis of new D-seco-C-nor-taxane derivatives in which the D-ring has been deleted and the C-ring has been transformed into a new pentatomic ring, i.e., the polyfunctionalized tetrahydrofuranosyl and cyclopentenyl or cyclopentyl ring, was performed starting from baccatin III derivatives. The synthetic strategy adopted took advantage of the oxetane ring opening and disconnection of the C4-C5 bond, followed by an intramolecular condensation. The formation of furanosyl or cyclopentyl rings is strictly dependent on the presence of unprotected or protected oxygen at C-7 in the starting material. The reactions proceeded with good diastereoselectivity with control of the stereochemistry of one or two stereocenters. 相似文献
10.
11.
Cheng-Ji Li Fan Xia Wen Zhang Kou Wang Gang Xu Hong-Bo Qin 《Tetrahedron letters》2018,59(26):2607-2609
Miltirone, 1,2-dehydromiltirone, saligerone have been synthesized form carnosic acid. Among them, one step transformation of carnosic acid into miltirone was realized when decarboxylation/aromatization was promoted by Lewis acid. Moreover, 4 derivatives exhibited potent cytotoxic activities against three human cancer lines in vitro. 相似文献
12.
Kun Fang Guo-Qiang Dong Hai Gong Na Liu Zhen-Gang Li Shi-Ping Zhu Zhen-Yuan Miao Jian-Zhong Yao Wan-Nian Zhang Chun-Quan Sheng 《中国化学快报》2014,25(7):978-982
A series of novel E-ring modified evodiamine derivatives were designed and synthesized as antitumor agents. Their capacity to interfere with the catalytic activity of topoisomerase Ⅰ and Ⅱ was evaluated by the relaxation assay. In vitro antitumor activity results revealed that compound 12 showed good antitumor activity with a broad spectrum. Its binding modes with topoisomerase Ⅰ and Ⅱ were clarified by molecular docking. 相似文献
13.
Seventy novel benzoylphenylurea compounds were synthesized and their antitumor activities were examined in vivo against P388 leukemia. N-(2-Nitrobenzoyl)-N'-[4-(2-pyrimidinyloxy)phenyl]ureas showed the highest antitumor activities when dosed intraperitoneally or orally. Their structure-activity relationships were examined with particular focus on the position and the variety of substituent on each aryl ring. 相似文献
14.
It is shown that 2-methyl-3-carbethoxy-4H,8H,5,6-dihydrothieno[2,3-d]thia[1]pyrano [4,3-b]pyrrole and 8-methyl-9-carbethoxy-10H,5,6-dihydrothieno[2,3-d]thia[1]chromeno[4,3-b]pyrrole and their S,S-dioxides, respectively, are obtained in the reaction of 2-methyl-3-carbethoxy-4-thienylhydrazine with tetrahydro-4-thiopyrone, tetrahydro-4-thiopyrone S, S-dioxide, 4-thiochromanone, and 4-thiochromanone S,S-dioxide in the presence of an acid catalyst.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 195–196, February, 1979. 相似文献
15.
Sun L Geng X Geney R Li Y Simmerling C Li Z Lauher JW Xia S Horwitz SB Veith JM Pera P Bernacki RJ Ojima I 《The Journal of organic chemistry》2008,73(24):9584-9593
Novel macrocyclic paclitaxel congeners were designed to mimic the bioactive conformation of paclitaxel. Computational analysis of the "REDOR-Taxol" structure revealed that this structure could be rigidified by connecting the C14 position of the baccatin moiety and the ortho position of C3'N-benzoyl group (C3'BzN), which are ca. 7.5 A apart, with a short linker (4-6 atoms). 7-TES-14beta-allyloxybaccatin III and (3R,4S)-1-(2-alkenylbenzoyl)-beta-lactams were selected as key components, and the Ojima-Holton coupling afforded the corresponding paclitaxel-dienes. The Ru-catalyzed ring-closing metathesis (RCM) of paclitaxel-dienes gave the designed 15- and 16-membered macrocyclic taxoids. However, the RCM reaction to form the designed 14-membered macrocyclic taxoid did not proceed as planned. Instead, the attempted RCM reaction led to the occurrence of an unprecedented novel Ru-catalyzed diene-coupling process, giving the corresponding 15-membered macrocyclic taxoid (SB-T-2054). The biological activities of the novel macrocyclic taxoids were evaluated by tumor cell growth inhibition (i.e., cytotoxicity) and tubulin-polymerization assays. Those assays revealed high sensitivity of cytotoxicity to subtle conformational changes. Among the novel macrocyclic taxoids evaluated, SB-T-2054 is the most active compound, which possesses virtually the same potency as that of paclitaxel. The result may also indicate that SB-T-2054 structure is an excellent mimic of the bioactive conformation of paclitaxel. Computational analysis for the observed structure-activity relationships is also performed and discussed. 相似文献
16.
[reaction: see text] Novel C2-C3'N-linked macrocyclic taxoids are synthesized using intramolecular Heck reaction in the key step. Macrocyclization proceeds with high regioselectivity in good yield. Taxoids bearing an olefin moiety at C2 and an iodide at C3'N give exo-products exclusively. However, the endo-products are formed with up to 100% regioselectivity just by switching the positions of the olefin and the iodide moieties. Some of these macrocyclic taxoids are significantly cytotoxic. 相似文献
17.
Bernard Bonnaud Dennis Bigg Jean-Franois Patoiseau 《Journal of heterocyclic chemistry》1991,28(8):1927-1932
The reaction of a number of γ-butyrolactones with azole anions is shown to give γ-substituted butanoic acids in moderate to good yields. The pyrrolyl and indolylbutanoic acids obtained underwent cyclization in a simple one-pot procedure employing ethyl chloroformate and boron trifluoride etherate. Some aspects of the chemistry of the resulting indolizin-8-ones are described. 相似文献
18.
Hubert Hřebabecký Milan Dejmek Martin Dračínský Michal Šála Pieter Leyssen Johan Neyts Martina Kaniaková Jan Krůšek Radim Nencka 《Tetrahedron》2012,68(4):1286-1298
Azanorbornylpurine derivatives were prepared by Mitsunobu reaction of appropriate hydroxyazanorbornane derivative with 6-chloropurine or construction of purine base at azanorbornylamines. The prepared target compounds were evaluated for antiviral activity and effect on neuronal and muscle nicotinic acetylcholine receptors. 相似文献
19.
Yangen Huang 《Tetrahedron》2004,60(38):8341-8346
Fluorous glycol derivatives 5 were prepared and evaluated as reagents for the protection of carbonyl groups for use in fluorous synthesis. The acetals formed from fluorous diol 5b (Rf=n-C8F17) with carbonyl compounds can be separated and purified by simple fluorous-organic extraction. 相似文献
20.
As part of a wider programme to identify novel photosensitizers for photodynamic therapy, the ability of a number of phthalocyanine dyes, including some novel copper phthalocyanine derivatives with a range of water solubilities, to produce potentially cytotoxic species in solution was examined. The experiments were performed in dimethylformamide using 1,3-diphenylisobenzofuran (DPIBF) as the scavenger. The study revealed that all the dyes tested produced DPIBF photobleaching on illumination in vitro, but with widely different (greater than 12x) rates. The possible correlation of DPIBF photobleaching rates with a number of the dyes' properties is discussed. 相似文献