Two New Compounds Isolated from<em> Liriope muscari</em>

Two new compounds, (2S,3R)-methyl 7-hydroxy-2-(4-hydroxy-3-methoxy-phenyl)-3-(hydroxymethyl)-2,3-dihydrobenzofuran-5-carboxylate (1) and (4R,5S)-5-(3-hydroxy-2,6-dimethylphenyl)-4-isopropyldihydrofuran-2-one (2), tentatively named norcurlignan and limlactone, respectively, were isolated from Liriope muscari, together with the known compound (-)-pinoresinol (3). The structures of these compounds were elucidated and characterized on the basis of 1D NMR, 2D NMR, CD and MS data. The in vitro antioxidant activities of compounds 1-3 were assessed by the DPPH and ABTS scavenging methods.     

Synthesis and voltammetric study of some new macrocyclic sulfur compounds for use as chelating agents for separation of arsenic (III) in wastewater and as molluscicidal agents against Biomophalaria Alexandrina Snails

A series of some new nanomeric molecules of cyclic 5- methoxy -5, 6–diaryl -4,5-dihydro -2H-1,2,4–triazin -3-thiones (1-3) has been synthesized. The interaction of compounds 1-3 with HgCl₂ in 1:1 and 1:2 molar ratios was used for the synthesis of the macrocyclic Schiff base [5,6, 11,12 - tetraaryl -1,2,4,7,8,10- hexa-aza cyclododoeca -4,6,10,12- tetraene -3,9-dithione] (4), macrocyclic thioethers 5 and/or complex 6. Chemical structures of the compounds were determined from elemental analysis and spectral measurements. The compounds were screened as molluscicidal agents against Biomophalaria Alexandrina Snails which cause Bilhariziasis. Cyclic voltammetry of selected compounds showed well-defined irreversible electrode couple suggesting application of these compounds as chelating agents for separation of arsenic in industrial wastewater samples. Compound 1 was physically immobilized onto polyurethane foams (PUFs) and was successfully used for complete removal of arsenic (III) & (V) species from wastewater.     

Microwave-induced and conventional heterocyclic synthesis: An antimicrobial entites of newer quinazolinyl-Δ2-pyrazolines

Heterocyclic compounds containing pyrazolines were reported to possess significant biological activity. Synthesis of 2-(ω-chloroacetonyl)-3-p-fluorophenyl-6-bromoquinazoline-4(3H)-ones (2), 2-(ω-hydrazinoacetonyl)-3-p-fluorophenyl-6-bromoquinazoline-4(3H)-ones (3) and 1′-[3H-3-p-fluorophenyl-4-oxo-6-bromoquinazoline-2-acetonyl]-3′-[1-o-chlorophenyl-3-methyl-5-azomethine-2-pyrazolidene]-5′-(substituted phenyl)-Δ²-pyrazolines (4a–j) have been described. Some of the new compounds were tested against bacteria (Gram –ve and Gram +ve) and fungi.     

Construction,molecular docking,antimicrobial and antioxidant activity of some novel 3-substitued indole derivatives using 3-Acetyl indole

This dissertation presents a method for the synthesis of substituted indoles bearing heterocyclic substituent in the 3- position. The route for the synthesis of the heterocyclic substituents indoles starts from the 3-acetyl indole nucleus. The reaction of 3-acetyl indole 1 with hydrazide compounds such as phenylhydrazine, hydrazine hydrate, and thio-semicarbazide, yields 3-(1-(2-phenylhydrazono) ethyl)-1H-indole 2, 3-(1-hydrazonoethyl)-1H-indole 6, and thiosemicarbazone 10, respectively. Thiophene-2-carboxaldeyde, isatine and 3-acetyl indole reacted with 3-(1-Hydrazonoethyl)-1H-indole 6. In the same way, 3-(1-(2-phenylhydrazono) ethyl)-1H-indole 2 reacted with thioglycollic acid, glycine and benzaldehyde. Thiosemicarbazone 10 reacted smoothly with acetic anhydride, piperidine, concentration of hydrochloric acid and thiophene-2-carboxaldeyde to provide the corresponding heterocycles. The reaction of 3-acetyl indole 1 with amine compounds such as p-nitroaniline formed Schiff base 15, which reacted with thioglycollic acid to give compound 16. 3-Acetyl indole 1 reacted with ethylene diamine to afford bis imine indole 17. The reports of the docking study revealed that the new compounds exhibit good antibacterial activity. The synthesized compounds screened in vitro for their antibacterial activity revealed remarkable inhibitory effects on the selected microorganisms. Besides, the antioxidant activity of some newly designed compounds has been investigated. The structures of the newly synthesized compounds are examined by spectral data (IR, ¹HNMR, ¹³C NMR and mass spectra).     

Novel benzimidazole derivatives as anti-cervical cancer agents of potential multi-targeting kinase inhibitory activity

Multi-target EGFR, HER2, VEGFR-2 and PDGFR is an improved strategy for the treatment of solid tumors. This work deals with synthesis of an array of new 6-benzoyl benzimidazole derivatives utlizing1-(6-benzoyl-2-(3,4-dimethoxyphenyl)-1H benzo[d] imidazol-1-yl)propan-2-one (1) as a starting compound. The new compounds were screened as cytotoxic agents against cervical cancer cells (Hela) and Doxorubicin served as a reference drug. Most of the tested compounds showed promising anticancer activity in addition to their safety towards the normal cell line. The most potent candidates were evaluated as EGFR, HER2, PDGFR-β and VEGFR2 inhibitors in comparison to Erlotinib. Compounds 9 and 13 exhibited promising suppression effects. Also, the latter compounds exhibited their ability to induce cellular apoptosis alongside cell cycle arrest at the G2/M phase and accumulation of cells in pre-G1 phase. Molecular docking analysis suggested that compounds 2c, 3f, 9, 12 and 13 tightly interacts with the amino acid residues in the active binding site of HER2 kinase.     

Synthesis,studies and in vitro antibacterial activity of some 5-(thiophene-2-yl)-phenyl pyrazoline derivatives

In the present investigation, a novel series of pyrazolines 2a–2d were synthesized by the cyclization of various -1-[2-(alkoxy) phenyl]-3-(thiophen-2-yl) prop-2-en-1-one 1a–1d with N-substituted phenyl hydrazine and thiosemicarbazide in the presence of CH₃COOH and NaOH in ethanol which lead to the formation of new pyrazolines. The structures of these compounds were elucidated by, IR, ¹H-NMR, ¹³C-NMR, ESI-MS spectral data and their purities were confirmed by elemental analyes. The in vitro antibacterial activity of these compounds was evaluated against two Gram-positive and two Gram-negative bacteria Aeromonas hydrophila, Yersinia enterocolitica, Listeria monocytogenes, and Staphylococcus aureus by microdilution method and then the minimum inhibitory concentration (MIC) of these compounds was determined. The results showed that compounds 1-[2-(benzyloxy) phenyl]-5-(thiophen-2-yl)-1-phenyl-4,5-dihydro-1H-pyrazol-4-yl (2b) and 1-[2-(naphthalen-2-ylmethoxy) phenyl]-5-(thiophene-2-yl)-1-phenyl-4,5-dihydro-1H-pyrazole-4-yl (2d) showed most promising antibacterial activity as compared to the antibiotics gentamicin and tetracycline in (Table 1, Table 2).     

A new dimeric imidazole alkaloid plasmid conjugation inhibitor from Lepidium sativum

Phytochemical investigation of the methanolic extract of Lepidium sativum seeds led to the isolation of a new compound, named 2-(3-(3-((1H-imidazol-2-yl)methyl)-5-methoxyphenoxy)benzyl)-1H-imidazole and given the trivial name Lepidine AK (1), along with three known compounds; Lepidine E (2), Lepidine B (3) and 2-(3-(2-((1H-imidazol-2-yl)methyl)-6-methoxyphenoxy)benzyl)-1H-imidazole (4). The structures were elucidated based on NMR spectroscopy, UV, IR and high-resolution electrospray ionization mass spectrometry. The isolated compounds were tested for bacterial conjugation inhibition. Lepidine AK (1, 100?μg/mL) reduced the conjugal transfer of the IncI₂ plasmid TP114 to 44.7?±?3.5% but interestingly promoted the conjugation of the IncN plasmid pKM101 to greater than 120%.     

Tubakialactones A–E,new polyketides from the endophytic fungus Tubakia sp. ECN-111

Three new isocoumarins and two new phthalides, tubakialactones A–E (1–5), together with three known polyketides including (R)-3,4-dihydro-4-hydroxyl-6,8-dimethoxy-4-methyl-3-methylene-1H-2-benzopyran-1-one (6), (?)-5,7-dimethoxy-3-methyl-1(3H)-isobenzofuranone (7), and isosclerone (8) were found in the endophytic fungus Tubakia sp. ECN-111 isolated from the leaves of Houttuynia cordata. The chemical structures of the new compounds were determined by spectroscopic analyses, including extensive 2D-NMR experiments. The absolute configuration of 3 and 7 was determined by optical rotation and circular dichroism.     

Novel NMR chiral solvating agents derived from (1R,2R)-diaminocyclohexane: synthesis and enantiodiscrimination for chiral carboxylic acids

A series of new compounds, (1R,2R)-1-(1′,8′-naphthalimide)-2-aminocyclohexane 1 and its 4′-derivatives 2 and 3 derived from (1R,2R)-1,2-diaminocyclohexane have been synthesized conveniently and efficiently. ¹H NMR spectroscopy was employed to investigate their enantiodiscriminating ability. Compared with α-phenylethylamine, a commercially available chiral solvating agent (CSA), these compounds exhibited better enantiodiscriminating ability toward the chiral carboxylic acids we had chosen, distinguishing them as promising and practical CSAs.     

Humulene derivatives from Saharian Asteriscus graveolens

Three new sesquiterpene-humulenes, (?)- asteriscunolides I (1), J (2) and (?)-(2Z,6E,9Z)-8-oxo-1α-acetoxy-2,6,9-humulatrien-12-oic acid (3) were isolated from the leaves-flowers of the Saharan medicinal plant Asteriscus graveolens along with six known compounds. The structures of the compounds were determined on the basis of spectroscopic mono and bidimensional NMR, mass spectrometry and by single-crystal X-ray diffraction. Compounds 1–3 were evaluated for cytotoxic assay, no significant activity was detected.     

Marine bacterial inhibitors from the sponge-derived fungus Aspergillus sp.

Chromatographic separation of a crude extract obtained from the fungus Aspergillus sp., isolated from the Mediterranean sponge Tethya aurantium, yielded a new tryptophan derived alkaloid, 3-((1-hydroxy-3-(2-methylbut-3-en-2-yl)-2-oxoindolin-3-yl)methyl)-1-methyl-3,4-dihydrobenzo[e][1,4]diazepine-2,5-dione (1), and a new meroterpenoid, austalide R (2), together with three known compounds (3–5). The structures of the new compounds were unambiguously elucidated on the basis of extensive one and two-dimensional NMR (¹H, ¹³C, COSY, HMBC, and ROESY) and mass spectral analysis. Interestingly, the compounds exhibited antibacterial activity when tested against a panel of marine bacteria, with 1 selectively inhibiting Vibrio species and 2 showing a broad spectrum of activity. In contrast, no significant activity was observed against terrestrial bacterial strains and the murine cancer cell line L5178Y.     

A novel plant growth regulator from Pholiota lubrica

Nine compounds including a new cinnamamide (1), N-(1-cinnamoylpyrrolidin-2-yl)cinnamamide, and two compounds (8 and 9) first isolated from natural sources, were obtained from the edible mushroom Pholiota lubrica. Their structures were determined by the interpretation of spectroscopic data. Compounds 1, 3 and 9 exhibited the inhibitory activity against lettuce, while compounds 2 and 7 promoted the growth of lettuce.     

Synthesis of new derivatized pyrazole based ligands and their catecholase activity studies

A synthesis of three new tripodal ligands: 3-[bis-(3,5-dimethyl-pyrazol-1-ylmethyl)-amino]-propan-1-ol L1, 3-[bis-(5-methyl-3-carbomethoxy-pyrazol-1-ylmethyl)-amino]-propan-1-ol, L2 and 3-[bis-(5-methyl-3-carboethoxy-pyrazol-1-ylmethyl)-amino]-propan-1-ol L3 is reported. The in situ-generated copper(II) complexes of three new compounds (L1–L3) were examined for their catalytic activities and were found to catalyse the oxidation reaction of catechol to o-quinone with the atmospheric dioxygen. These activities depend on the nature of the ligand and the copper salts.     

In vitro anthelmintic and cytotoxic activities of extracts from the stem barks of Berlinia confusa (C. Hoyle) and identification of its active constituents

Phytochemical investigation of EtOAc extract from the stem bark of Berlinia confusa yielded a new and two known polysaturated monoacylglycerides characterised as 1-O-docosanoyl-sn-glyceride (3), 1-O-(13-methyltetradecanoyl)-sn-glycerol (4) and 1-O-pentadecacanoyl-sn-glycerol (5); along with the known compounds betulinic acid (1) and sitosteryl-β-d-glucoside (2). The structures of these compounds were elucidated using analytical methods, including 1D and 2D-NMR together with MS spectroscopy. The extracts and isolated compounds demonstrated concentration-dependent anthelmintic activities against Fusciola gigantica (liver flukes) and Taenia solium (tapeworm) at 10–100 mg/ml. The extracts and isolated compounds were evaluated for cytotoxicity against a small panel of three human tumour cell lines.     

Pimprinols A–C,from the terrestrial actinomycete,Streptomyces sp.

A Streptomyces sp. Lv3-13, isolated from the rhizosphere soil of the plant Mespilus germanica, has yielded three new pimprinine derivatives, named pimprinols A–C (1–3) and the unknown (2-aminophenyl)(2-ethyloxazol-5-yl) methanone (4) along with the known compounds 2-ethyl oxazole pimprinine and 2-propyl oxazole pimprinine. The structures of the compounds were elucidated based on spectroscopic methods including UV, HR-ESIMS and 1D, 2D NMR data. Compounds 1–4 were screened for antimicrobial and cytotoxic activities.     

Design,synthesis and evaluation of 2-(4-(substituted benzoyl)-1,4-diazepan-1-yl)-N-phenylacetamide derivatives as a new class of falcipain-2 inhibitors

The cysteine protease, falcipain-2 is an important drug target in human malaria parasite Plasmodium falciparum. A new series of 2-(4-(substituted benzoyl)-1,4-diazepan-1-yl)-N-phenylacetamide derivatives 5(a–t) were designed as per pharmacophoric requirements of falcipain-2 inhibitors using ligand-based approach. The target compounds were synthesized from the key intermediate, 2-(1,4-Diazepan-1-yl)-N-phenylacetamide, by coupling it with appropriate carboxylic acids using carbodiimide chemistry. Structural features of target compounds were characterized by spectral data (¹H NMR, and mass) and elemental analyses. The purity of the final compounds was confirmed by HPLC. The compounds were tested for their in vitro falcipain-2 inhibitor activity on recombinant falcipain-2 enzyme. Five compounds 5b, 5g, 5h, 5j, 5k showed good inhibitory activity (>60%), against falcipain-2 at 10 μM concentration, and fifteen compounds showed weak to moderate inhibitor activity. Compound 5g, the most potent compound from this series showed 72% inhibition at 10 μM concentrations.     

Novel indan-1,3-dione derivatives: Design,green synthesis,effect against tomato damping-off disease caused by Fusarium oxysporum and in silico molecular docking study

An effective method for synthesizing series of twenty-two new compounds 1, 2a,b, 3, 4a,b, 5a-e, 7, 8, 9, 10, 12, 13a-d, 15a,b was performed starting from reaction of 1,2,3-indenetrione thiourea, and ethyl cyanoacetate under microwave irradiation and / or 2-(1,3-dioxo-1H-inden-2(3H)-ylidene) hydrazine carbothioamide with acetic anhydride. Chemical structure of the obtained products has been established by spectroscopic techniques including FTIR, ¹H NMR, ¹³C NMR, DEPT-135, and mass spectroscopy. The designed new compounds have been successfully examined in-vitro for their antifungal activities. The relation between the structure of the synthesized compounds and their activity against tomato damping-off disease caused by Fusarium oxysporum fungi was studied and favourable results were obtained. The antifungal studies indicated that compounds 1, 7, 4a and 5a-d exerted the highest antifungal activities, while 3 and 4b recorded the lowest effect. The obtained results confirmed the possibility of the application of ethyl 6′-amino-1,3-dioxo-2′-thioxo-1,2′,3,3′-tetrahydro-1′H-spiro[indene-2,4′-pyrimidine]-5′-carboxylate 1 as a new effective regulator of the vegetative growth of tomatoes. The molecular docking analysis was performed within succinate dehydrogenase (SDH) as a target enzyme in order to rationalize the promising findings obtained for the active compounds 1, 2a,b, 5a-d, 7, 8, 9, 10, 12, and 13a.     

Biogenetically related caged ent-kaurane diterpenoids from Isodon eriocalyx var. laxiflora

Two novel caged ent-kauranoids, neolaxiflorins D (1) and E (2), along with three other new ent-kauranoids, neolaxiflorins F–H (3–5), and a known one, eriocalyxin B (6), were obtained from Isodon eriocalyx var. laxiflora. Neolaxiflorin D (1) is the first 15,16-seco-16,17-dinor-ent-kaurane diterpenoid, and neolaxiflorin E (2) is the first 15,16-seco-17-homo-ent-kauranoid. The absolute configurations of ent-kauranoids 1 and 2 were determined by single-crystal X-ray diffraction analyses. Structural analysis of intermediate compounds 3–5 indicated that eriocalyxin B (6) is a biogenetic precursor of caged ent-kauranoids 1 and 2 as illustrated. The cytotoxic activity of the new compounds was evaluated by an MTT assay.     

Synthesis and insecticidal evaluation of novel sulfide-containing amide derivatives as potential ryanodine receptor modulators

With the aim of discovering new bioactive pesticides for crop protection, a series of novel sulfidecontaining amide derivatives A were efficiently synthesized via a strategy of modifying the “amide” structure of anthranilic diamide insecticides. The single-crystal structures of A2-3 and A4-5 were firstly reported. The bioassay results showed that most of the synthesized compounds display moderate to high insecticidal activities. Particularly, some sulfone-containing compounds, e.g., A2-3, A3-3 a...     

Two xanthones and two rotameric (3⟶8) biflavonoids from the Cameroonian medicinal plant Allanblackia floribunda Oliv. (Guttiferae)

Two xanthones, 2-(3-hydroxy-3,3-dimethyldihydroallyl)-dihydro-6-deoxyisojacareubin (1) and dihydro-6-deoxyjacareubin (2), and two 3 ⟶ 8 rotameric biflavonoids, (2R,3S)-volkensiflavone-7-O-β-acetylglucopyranoside (3) and (2S,3S)-morelloflavone-7-O-β-acetylglucopyranoside (4), together with fifteen known compounds, were isolated from a dichloromethane/methanol (1:1, v/v) extract of the bark of the plant Allanblackia floribunda. The structures of the new compounds were elucidated by NMR spectroscopy and mass spectroscopic techniques and those of the known ones were deduced by comparison with data reported in the literature. The isolated biflavonoids were obtained as mixtures of conformers exhibiting duplicate NMR signals in solution at 25 °C and their respective absolute configurations were assigned using circular dichroism spectroscopy. Selected isolated compounds were assessed for their antibacterial and antioxidant properties.