- Synthesis and cytotoxic activities of novel 4-methoxy-substituted and 5-methyl-substituted (3′S,4′S)-(-)-cis-khellactone derivatives that induce apoptosis via the intrinsic pathway
-
This study deals with the design and synthesis of a series of novel 4-methoxy-substituted and 5-methyl-substituted (3′S,4′S)-(-)-cis-khellactones. The newly synthesized compounds were characterized by1H nuclear magnetic resonance (NMR),13
- Chen, Jingrun,Liu, Junjie,Cui, Dongxiao,Yan, Chaoqun,Meng, Liqiang,Sun, Liqian,Ban, Shurong,Ge, Rui,Liang, Taigang,Li, Qingshan
-
p. 1891 - 1904
(2017/07/06)
-
- Ytterbium triflate promoted coupling of phenols and propiolic acids: Synthesis of coumarins
-
Coumarins are a well-known class of natural occurring and semi-synthetic products with reported important and effective pharmacological activities. In this Letter an improved method for the chemical synthesis of such compounds is described. Coumarins have been obtained in good to excellent yields under microwave irradiation and solvent-free conditions in a short time from differently substituted phenols and propiolic acids used as starting materials in the presence of Yb(OTf)3 hydrate 10% mol as the catalyst.
- Fiorito, Serena,Epifano, Francesco,Taddeo, Vito A.,Genovese, Salvatore
-
supporting information
p. 2939 - 2942
(2016/06/14)
-
- A catalyst-free one-pot construction of skeletons of 5-methoxyseselin and alloxanthoxyletin in water
-
In refluxing water and without an additional catalyst, electron-rich phenols could react with alkynoic acids or alkynoates to provide coumarin structures. The skeletons of two natural pyranocoumarins, 5-methoxyseselin and alloxanthoxyletin, could be constructed (total yield up to 76%) in an aqueous multicomponent reaction in which isoprenyl acetate, propiolic acid, and phloroglucinol were simply mixed and refluxed in water.
- Cao, Jin-Li,Shen, Su-Li,Yang, Peng,Qu, Jin
-
supporting information
p. 3856 - 3859
(2013/09/02)
-
- Synthesis and anti-inflammatory effects of a series of novel 7-hydroxycoumarin derivatives
-
A number of 7-hydroxycoumarins have been synthesised by Pechmann cyclisation using differently substituted resorcinols employing perchloric acid as the condensing agent. All the compounds have been characterised by analytical and spectroscopic methods. The anti-inflammatory properties were tested with LPS-induced inflammation in J774 macrophages. Expression of iNOS and COX-2 was determined by Western blot, NO by nitrite assay and IL-6 by ELISA analyses. Fifteen of the tested 7-hydroxycoumarins also inhibited IL-6 production but none of them had any major inhibitory effect on COX-2 expression.
- Timonen, Juri M.,Nieminen, Riina M.,Sareila, Outi,Goulas, Antonis,Moilanen, Lauri J.,Haukka, Matti,Vainiotalo, Pirjo,Moilanen, Eeva,Aulaskari, Paula H.
-
supporting information; experimental part
p. 3845 - 3850
(2011/11/13)
-
- Structural modification of a specific antimicrobial lead against Helicobacter pylori discovered from traditional Chinese medicine and a structure-activity relationship study
-
Psoralen (1a) was found to be a specific and potent antimicrobial lead against Helicobacter pylori (H. pylori) from a traditional Chinese medicine (TCM) in the bioassay directed isolation. A series of structurally diverse analogues of 1a were thus designed and synthesized to improve the antimicrobial potency, some of which showed more potent activities than the lead compound (1a) against H. pylori. Among them, compound 25a is 16-fold stronger (MIC = 0.39 μg/mL) than 1a (MIC = 6.25 μg/mL), and is even potent than the positive control metronidazole (MIC = 0.50 μg/mL). The in vitro antimicrobial activities against H. pylori of these structurally diverse analogues based on the scaffold of 1a have also led to an outline of structure-activity relationship.
- Zhang, Bang-Le,Fan, Cheng-Qi,Dong, Lei,Wang, Fang-Dao,Yue, Jian-Min
-
supporting information; experimental part
p. 5258 - 5264
(2011/01/04)
-
- Synthesis of hydroxycoumarins and hydroxybenzo[f]- or [h]coumarins as lipid peroxidation inhibitors
-
Substituted hydroxycoumarins and 7- or 8-hydroxybenzo[f]coumarins were prepared by the treatment of phenols and naphthalenediols, respectively, with malic acid and H2SO4 under microwave irradiation. 7- or 8-Hydroxybenzo[f]coumarins and 6-hydroxybenzo[h]coumarin were synthesized by the reaction of naphthalenediols with ethylpropiolate in the presence of ZnCl2 in refluxing dioxane. The compounds were tested in vitro for their ability: (i) to interact with 1,1-diphenyl-2-picryl-hydrazyl (DPPH) stable free radical, (ii) to inhibit lipid peroxidation, (iii) to scavenge the superoxide anion, (iv) to inhibit the activity of soybean lipoxygenase and (v) to inhibit in vivo the carrageenin-induced rat paw edema. Most of them are potent superoxide anion scavengers and inhibit in vitro lipid peroxidation. The majority of the compounds did not show high lipoxygenase inhibitory activity. No differences were observed between biological responses of hydroxycoumarins and hydroxybenzocoumarins. Compound 3i was found to present a promising antioxidant profile.
- Symeonidis, Theodoros,Chamilos, Michael,Hadjipavlou-Litina, Dimitra J.,Kallitsakis, Michael,Litinas, Konstantinos E.
-
experimental part
p. 1139 - 1142
(2009/08/07)
-
- Design, synthesis, and 3D QSAR of novel potent and selective aromatase inhibitors
-
The design, synthesis, and biological evaluation of a series of new aromatase inhibitors bearing an imidazole or triazole ring linked to a fluorene (A), indenodiazine (B), or coumarin scaffold (C) are reported. Properly substituted coumarin derivatives di
- Leonetti, Francesco,Favia, Angelo,Rao, Angela,Aliano, Rosaria,Paluszcak, Anja,Hartmann, Rolf W.,Carotti, Angelo
-
p. 6792 - 6803
(2007/10/03)
-
- Anti-AIDS agents. 37. Synthesis and structure-activity relationships of (3'R,4'R)-(+)-cis-khellactone derivatives as novel potent anti-HIV agents
-
To explore the structural requirements of (+)-cis-khellactone derivatives as novel anti-HIV agents, 24 monosubstituted 3',4'-di-O-(S)- camphanoyl-(+)-cis-khellactone (DCK) derivatives were synthesized asymmetrically. These compounds included 4 isomeric monomethoxy analogues (3- 6), 4 isomeric monomethyl analogues (7-10), 4 4-alkyl/aryl-substituted analogues (11-14), and 12 4-methyl-(+)-cis-khellactone derivatives (15-26) with varying 3',4'-substituents. These (+)-cis-khellactone derivatives were screened against HIV-1 replication in acutely infected H9 lymphocytes. The results demonstrated that the (3'R,4'R)-(+)-cis-khellactone skeleton, two (S)-(-)-camphanoyl groups at the 3'- and 4'-positions, and a methyl group on the coumarin ring, except at the 6-position, were optimal structural moieties for anti-HIV activity. 3-Methyl- (7), 4-methyl- (8), and 5-methyl- (9) 3',4'- di-O-(S)-camphanoyl-(3'R,4'R)-(+)-cis-khellactone showed EC50 and therapeutic index values of -5 μM and >2.15 x 106, respectively, in H9 lymphocytes, which are much better than those of DCK and AZT in the same assay. Furthermore, 8 and 9 also showed potent inhibitory activity against HIV-1 replication in the CEM-SS cell line, and most monosubstituted DCK analogues were less toxic than DCK in both assays.
- Xie, Lan,Takeuchi, Yasuo,Cosentino, L. Mark,Lee, Kuo-Hsiung
-
p. 2662 - 2672
(2007/10/03)
-
- Anti-AIDS agents 33.1 Synthesis and anti-HIV activity of mono-methyl substituted 3',4'-di-O-(-)-camphanoyl-(+)-cis-khellactone (DCK) analogues
-
Four isomeric methyl substituted DCK analogues (2-5) were asymmetrically synthesized from different starting materials. 3-Methyl, 4-methyl, and 5- methyl-3',4'-di-O-(-)-camphanoyl-(+)-cis-khellactone (2 -4) all were extremely potent against HIV-1 replication in H9 lymphocyte cells with EC50 and therapeutic index values of -7 μM and >3.72 x 108, respectively, which are much better than those of DCK and AZT in this assay.
- Xie, Lan,Takeuchi, Yasuo,Cosentino, L. Mark,Lee, Kuo-Hsiung
-
p. 2151 - 2156
(2007/10/03)
-
- Furocoumarin for the photochemotherapy of psoriasis and related skin diseases
-
A class of alkyl-substituted angular flurocoumarins, sometimes termed alkylangelicins, useful in the photochemotherapy of psoriasis and in other skin diseases characterized by cellular hyperproliferation or lack of skin pigmentation is disclosed for topical application or systemic administration. Compared with conventional psoralens the described compounds exhibit a lower risk of skin cancer, absence of phototoxicity problems anderithema to the patient so treated. One preferred compound is 5-methylangelicin.
- -
-
-
- Synthesis of some photosensitizing methylangelicins, as monofunctional reagents for DNA
-
angelicins methylated angelicans were synthesized for obtaining monofunctional reagents for DNA; these compounds may present some interest with regard to the development of useful drugs in photochemotheapy. The new derivatives photobind covalently to DNA, however, they are unable to produce inter-strand, cross-linkages in the macromolecule. Thephotobiological activity was tested on phage T2 and was higher for the methylated derivatives than for angelicin.
- Guiotto,Rodighiero,Pastorini,et al.
-
p. 489 - 494
(2007/10/02)
-