Unusual Spirodecane Sesquiterpenes and a Fumagillol Analogue from Cordyceps ophioglossoides

Investigation of the cultured mycelia of Cordyceps ophioglossoides resulted in the isolation and characterization of three new unusual spiro[4.5]decane sesquiterpenes, cordycepol A ( 1 ), cordycepol B ( 2 ), and cordycepol C ( 3 ), and a new fumagillol analogue, cordycol ( 4 ). Their structures were established by spectroscopic means. The cytotoxic activities were also evaluated, compounds 3 and 4 showing their IC₅₀ values in the range of 12–33 μg/ml against HeLa and HepG2 (Table 3). In addition, 3 and 4 were not obviously harmful towards normal liver cell lines LO2, showing IC₅₀ values above 80 μg/ml.     

Five New Cycloartane‐Type Triterpenoid Saponins from Nervilia fordii

Five new cycloartane glycosides, nervisides D–H ( 1 – 5 ), were isolated from the AcOEt‐ and H₂O‐soluble portions of the 90% EtOH extract of the aerial part of the plant Nervilia fordii. The structures of the isolated glycosides were elucidated by extensive spectroscopic analysis including HR‐ESI‐MS and NMR data. The isolated nervisides D–H were evaluated for the cytotoxic activity in vitro against human‐tumor cell lines (CNE, Hep‐2 and HepG2) with the MTT method.     

Doped Nano‐Sized Copper(I) Oxide (Cu2O) on Melamine?Formaldehyde Resin: a Highly Efficient Heterogeneous Nano Catalyst for ‘Click’ Synthesis of Some Novel 1H‐1,2,3‐Triazole Derivatives Having Antibacterial Activity

A facile and simple protocol for the 1,3‐dipolar cycloaddition of organic azides with terminal alkynes catalyzed by doped nano‐sized Cu₂O on melamine? formaldehyde resin (nano‐Cu₂O? MFR) as a new and convenient heterogeneous catalyst is described. In this method, ‘click’ cycloaddition of various structurally diverse β‐azido alcohols and alkynes in the presence of nano‐Cu₂O? MFR in H₂O/THF 1 : 2 furnished the corresponding 1,4‐disubstituted 1H‐1,2,3‐triazole adducts 1a – 1o in good to excellent yields at room temperature (Scheme and Table 3). The nano‐Cu₂O? MFR was characterized by scanning electron microscopy (SEM), X‐ray diffraction (XRD), inductively coupled plasma (ICP) analysis, and FT‐IR. The nano‐Cu₂O? MFR could be easily recovered and recycled from the reaction mixture and reused for many consecutive trials without significant decrease in activity (Table 4). The in vitro antibacterial activities of all synthesized compounds were tested on several Gram‐positive and/or Gram‐negative bacteria (Table 5). The results demonstrate the promising antibacterial activity for some of the synthesized compounds.     

Convenient synthesis and antitumor evaluation of some new 9-ethyl-3-(hetaryl)carbazoles

Abstract

In continuing our efforts to develop new potent anticancer candidates, a new series of 9-ethylcarbazoles carrying at position 3 various heterocyclic substituents such as 2-imino-2H-chromenes 5a–e, 2-oxo-2H-chromenes 6a–e, 3-imino-3H-benzo[f]chromene 8, 3-oxo-3H-benzo[f]chromene 9, 2-pyridones 11, 14, pyrazole 19, pyrimidine 23, pyrido[1,2-a]pyrimidine 27, 2H-pyran-2-one 30, and pyrano[2,3-d]pyrimidinetrione 34 were efficiently synthesized, characterized and evaluated for their in vitro antitumor activity. The mechanism for the synthesis of compounds was also discussed. Most of the synthesized compounds were displayed the considerable anticancer activities against three human tumor cells lines, in particular, colon carcinoma (HCT-116), hepatocellular carcinoma (HepG-2) and breast cancer (MCF-7). Compound 6d proves as most active molecule in this study with special effectiveness against the human HCT-116 and HepG-2 as its IC₅₀ values are 1.50, 0.90?μM, respectively, when doxorubicin is compared. Compound 34 was also found to have high activity against HepG-2, HCT-116 and moderate activity against MCF-7.     

The cytotoxic activities of imidazole derivatives prepared from various guanylhydrazone and phenylglyoxal monohydrate

Abstract

A series of imidazole derivatives were synthesized from two-component condensation reaction of phenylgloxal monohydrate with guanylhydrazone. They were characterized by spectroscopic and analytical techniques. The in vitro anticancer evaluation of these compounds was done on human breast cancer (MCF-7) and human liver cancer (HepG2) cell lines using the MTT assay method. Most of the newly synthesized compounds displayed cytotoxic activity against these cancerous cells. In fact, compounds 3a, 3e, and 3?h exhibited more cytotoxic activities than the positive control drugs, fluro-5, and irinocam, against the MCF-7 cell line. Almost all the compounds, except for three, 3b, 3d, and 3f, gave more cytotoxic results than cisplatin. Therefore, these compounds could be considered for further development as anticancer drug candidates.     

Modified Pyridine-Substituted Coumarins: A New Class of Antimicrobial and Antitubercular Agents

Some new biologically potent coumarin derivatives 7a–f, 8a–f, and 9a–f bearing modified pyridine moieties (indeno[1,2-b]pyridine, 4-azaphenanthrene and benzofuro [3,2-b]pyridine) at the sixth position were designed and synthesized. All the synthesized compounds were assayed for their antimicrobial efficiency against Staphylococcus aureus, Bacillus subtilis, Escherichia coli, Salmonella typhi, Candida albicans, and Aspergillus niger. Most of the compounds showed appreciable antimicrobial activity against the tested strains. Compounds 8b, 8c, 9b, 9d, and 9f emerged as most proficient members of the series. The antitubercular activity for all the synthesized compounds was performed against Mycobacterium tuberculosis H37R_v. Compounds 8f, 9b, and 9f exhibited promising antitubercular activity. Consequently, synthesized derivatives were found to be worthy of further investigation.     

New N-Substituted (E)-4-Arylidene Isoquinoline-1,3-dione Derivatives: NMR Spectroscopic Investigation and Antibacterial Activity

Abstract

New N-substituted 4-arylidene-isoquinoline-1,3-dione derivatives were obtained as one geometrical isomer by aldol condensation of the appropriate aldehyde and the corresponding N-substituted homophthalimides. The structural elucidation of compounds 3a–h was established by infrared and NMR spectroscopy including ¹ Dimmock , J. R. ; Wong , M. L. C. Bioactivities and potential uses in drug design of acyclic α,β-unsaturated ketones . Can. J. Pharm. Sci. 1976 , 11 , 35 – 53 .[Web of Science ®] , [Google Scholar]H, ¹³ Perjési , P. ; Szabó , D. ; Batta , G. ; Földesi , A. The stereochemistry of reaction of 2-benzylidenecyclohexanone with dithiocarbamic acid . Tetrahedron Lett. 1987 , 28 , 571 . [Google Scholar]C, CH CORR, and distortionless enhancement by polarization transfer measurements. Compounds 3d–h were evaluated for their antibacterial activity against some strains of bacteria using the disc diffusion method and microdilution tests.     

Silica Sulfuric Acid: An Efficient,Reusable, Heterogeneous Catalyst for the One-Pot,Five-Component Synthesis of Highly Functionalized Piperidine Derivatives

A series of highly functionalized piperidine derivatives was synthesized through one-pot, five-component reaction of aldehydes, amines, and β-ketoesters. Silica sulfuric acid efficiently catalyzes the reaction to afford the corresponding piperidine derivatives in good yields. As a representative example, heating of 4-methylaninle, 4-fluorobezaldehyde, and methyl-acetoacetate in methanol in the presence of silica sulfuric acid furnished the corresponding ethyl 2,6-bis(4-fluorophenyl)-1-p-tolyl-4-(p-tolylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate in excellent yield (85%). Most of the synthesized compounds were screened in vitro for their antibacterial and antifungal activities. Most of compounds showed significant antibacterial activity.     

Phytochemical Investigation by Microwave‐Assisted Extraction of Essential Oil of the Leaves of Walnut Cultivated in Algeria

Walnut (Juglans regia L.) leaves are used traditionally as an herbal tea indicated for non‐insulin‐dependent diabetics. In recent years, the type‐II diabetes is occurring worldwide with increasing frequency. Thus, there is an urgent need to explore the new beneficial biomolecules on the human health. Our objective was to investigate, for the first time, the volatiles profile of Juglans regia L. leaves from Algiers region. The extraction of essential oil of fresh plant material was performed by microwave‐assisted hydrodistillation (MAHD), for the first time, a relatively recent method, then by the conventional hydrodistillation technique (HD) for comparison. The collected extracts were analyzed by GC‐FID and GC/MS using two capillary columns with different polarity. Extraction time of 1 h by MAHD provided higher yields (0.050±0.001% (w/w)) than by HD (0.030±0.006% (w/w)) after 3 h. A total of 38 compounds were identified using both techniques. Essential oils had similar qualitative but different quantitative composition in terms of chemical compounds. The MAHD method improved yield while reducing the extraction time. The sesquiterpenes were the dominant family in both MAHD and HD essential oils with β‐caryophyllene being the major constituent. Monoterpenes, including hydrocarbon and oxygenated, prevail in HD volatile fraction with β‐pinene and eucalyptol, respectively, as major components.     

New Cytotoxic Triterpenoids from the Aerial Parts of Euphorbia sieboldiana

Phytochemical investigation of the EtOH extract of Euphorbia sieboldiana led to the isolation of four new oleanane‐type triterpenoids, (1β,2α,3β,19β)‐1,2,3,19‐tetrahydroxyolean‐12‐en‐28‐oic acid, (1β,3β,19β)‐1,3,19‐trihydroxyolean‐12‐en‐28‐oic acid, (1β,2α,3β,16β,19β)‐1,2,3,16,19‐pentahydroxyolean‐12‐en‐28‐oic acid, and (1β,2α,3β,19β,23)‐1,2,3,19,23‐pentahydroxyolean‐12‐en‐28‐oic acid, along with 16 known compounds. Their structures were established by extensive 1D‐ and 2D‐NMR, as well as other spectral analyses. Biological evaluation of the four new triterpenoids revealed potent cytotoxic activities against HeLa and Hep‐G2 cells.