- Design, Synthesis, and Bioactivities of Phthalide and Coumarin Derivatives Based on the Biosynthesis and Structure Simplification of Gossypol
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Because gossypol and hemigossypol show antiviral activity but are structurally complex, we designed and synthesized a series of structurally simpler phthalide and coumarin derivatives. The phthalide derivatives were synthesized by opening the naphthalene ring of hemigossypol, and the coumarin derivatives were synthesized by ring-opening reactions of the phthalide derivatives with the goal of investigating the effect of the lactone ring size on bioactivity. The bioassay results showed that the two series of target compounds possessed moderate to good activities against tobacco mosaic virus, One of the compounds showed in vivo inactivation, curative, and protection activities of 50 ± 1, 53 ± 3, and 48 ± 2% at 500 mg/L, values which are higher than those of gossypol (32 ± 1, 35 ± 1, 29 ± 1%, respectively) and comparable to those of hemigossypol (55 ± 1, 49 ± 1, and 48 ± 1%, respectively) and the commercial antiviral agent ningnanmycin (56 ± 2, 54 ± 1, 58 ± 1%) at the same dose. Thus, this compound is a promising candidate for the development of new anti-plant-virus agents. In addition, most of the synthesized compounds showed broad-spectrum activity when tested against 14 kinds of phytopathogenic fungi and showed selectivity against Sclerotinia sclerotiorum, Physalospora piricola, and Rhizoctonia cerealis. Moreover, some of the compounds exhibited activity against Plutella xylostella larvae; the two most active compounds exhibited larvicidal activities (LC50) of 4.10 and 5.47 mg/L, respectively. Further studies showed that these compounds also exhibited insecticidal activities against Mythimna separata, Helicoverpa armigera, and Pyrausta nubilalis larvae.
- Guo, Zhonglin,Zhou, Pan,Song, Hongjian,Liu, Yuxiu,Zhang, Jingjing,Li, Yongqiang,Wang, Qingmin
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p. 15123 - 15135
(2021/12/27)
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- Regioselective cyclization of 2-alkynylbenzoic acid in water for the synthesis of isocoumarin
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In this work, a regioselective synthesis of isocoumarins from 2-alkynylbenzoic acid is reported. The transformations proceed smoothly with good yields in water via a metal-free radical pathway. When catalytic TBAB is employed, the reaction provides various isocoumarin derivatives according to the structures of the corresponding precursors. It is believed that TBAB serves as a phase transfer catalyst and radical initiator in the reaction. Compared to previous methodologies, the synthetic procedure reported herein provides a more environmentally benign route for the synthesis of isocoumarins.
- Wang, Yan-Hua,Qiu, Guanyinsheng,Zhou, Hongwei,Xie, Wenlin,Liu, Jin-Biao
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supporting information
p. 3850 - 3855
(2019/06/17)
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- Tuning of photoluminescence properties of functional phthalides for OLED applications
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With an objective to develop simple organic systems and tailor their properties for optoelectronic applications, we have synthesized three functionalized phthalide derivatives and have investigated their electroluminescence and photophysical properties under different conditions. These derivatives showed good solubility in common organic solvents and exhibited strong absorption in the range 320–400?nm, having molar extinction coefficient values of ca. 104?M?1?cm?1. The monomeric solution of these derivatives exhibited very low fluorescence quantum yields (ΦF) of ca. 0.003–0.04 owing to their inherent structural features such as intramolecular free rotation and decay to the dark triplet states. However, upon complexation with Lewis acids, such as BCl3, these derivatives showed increased fluorescence quantum yields up to ca. 0.21?±?0.01 and also exhibited aggregation induced emission (AIE) in water/acetonitrile mixtures with the emission yields in the range ca. 0.11–0.16. The morphological analysis of the aggregates through SEM and TEM showed the formation of rod-like structures in 90% water/acetonitrile mixture with an average size of ca. 100?nm. Supporting the observed aggregation induced enhancement in emission properties, these derivatives also exhibited significantly enhanced solid state fluorescence quantum yields of ca. 0.58–0.60. As a representative example, organic light emitting diode (OLED) fabricated using the derivative 3 as the emissive layer showed an efficient electroluminescence centered at 524?nm with a turn on voltage of 9?V, demonstrating thereby their potential use in optoelectronic applications.
- Shanmugasundaram, Madhesh,Joseph, Joshy,Ramaiah, Danaboyina
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p. 156 - 162
(2016/08/15)
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- Improvement of antibacterial activity of some sulfa drugs through linkage to certain phthalazin-1(2H)-one scaffolds
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RAB1 5 is a lead antibacterial agent in which trimethoprim is linked to phthalazine moiety. Similarly, our strategy in this research depends on the interconnection between some sulfa drugs and certain phthalazin-1(2H)-one scaffolds in an attempt to enhance their antibacterial activity. This approach was achieved through the combination of 4-substituted phthalazin-1(2H)-ones 9a, b or 14a, b with sulfanilamide 1a, sulfathiazole 1b or sulfadiazine 1c through amide linkers 6a, b to produce the target compounds 10a-d and 15a-e, respectively. The antibacterial activity of the newly synthesized compounds showed that all tested compounds have antibacterial activity higher than that of their reference sulfa drugs 1a-c. Compound 10c represented the highest antibacterial activity against Gram-positive bacteria Streptococcus pneumonia and Staphylococcus aureus with MIC = 0.39 μmol/mL. Moreover, compound 10d displayed excellent antibacterial activity against Gram-negative bacteria Escherichia coli and Salmonella typhimurium with MIC = 0.39 and 0.78 μmol/mL, respectively.
- Ibrahim, Hany S.,Eldehna, Wagdy M.,Abdel-Aziz, Hatem A.,Elaasser, Mahmoud M.,Abdel-Aziz, Marwa M.
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p. 480 - 486
(2014/09/03)
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- Pd-free Sonogashira coupling: One pot synthesis of phthalide via domino Sonogashira coupling and 5-exo-dig cyclization
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Phthalides have been synthesized exclusively in one pot via Pd-free Sonogashira coupling. A Cu-catalyzed domino Sonogashira coupling and 5-exo-dig cyclization between suitable substituted ortho-bromobenzoic acids and terminal alkynes afforded phthalides in good yields under mild reaction conditions.
- Dhara, Shubhendu,Singha, Raju,Ghosh, Munmun,Ahmed, Atiur,Nuree, Yasin,Das, Anuvab,Ray, Jayanta K.
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p. 42604 - 42607
(2015/02/19)
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- Directing the regioselectivity of rhodium(I) catalysed cyclisation of 2-alkynyl benzoic acids
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Rhodium(I) dicarbonyl complexes 1-4 containing chelating N-donor ligands bis(pyrazolyl)methane (bpm), bis(imidazolyl)methane (bim), tris(pyrazolyl) toluidine (tpt) or tris(imidazolyl)methanol (tim) were investigated as catalysts for the hydroalkoxylation of alkynyl benzoic acids (5a-g). The regioselectivity of the reaction was shown to be highly dependent on the nature of the terminal alkyne substituent (R) of the alkynol substrate. It was also determined that the presence of a third uncoordinated N-donor group in complexes 3 and 4 suppressed the catalytic efficiency of these complexes, and that the selectivity of the reaction for forming either endocyclic (6) or exocyclic (7) hydroalkoxylation products was influenced by the pendant hydroxyl group present in complex 4. We used 13C NMR spectroscopy to quantify the polarity of the alkynyl benzoic acid C≡C bond and our efforts to correlate this measure of bond polarity to the observed regioselectivity of the reaction are discussed.
- Man, Bradley Y.-W.,Knuhtsen, Astrid,Page, Michael J.,Messerle, Barbara A.
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p. 248 - 252
(2013/10/22)
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- One-pot synthesis of phthalides via regioselective intramolecular cyclization from ortho-alkynylbenzaldehydes
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A one-pot synthesis of phthalides via an intramolecular 5-exo-dig cyclization of ortho-alkynylbenzaldehydes under mild NaClO2 oxidation conditions is described.
- Li, Jim,Chin, Elbert,Lui, Alfred S.,Chen, Lijing
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scheme or table
p. 5937 - 5939
(2010/11/21)
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- Catalytic enantioselective synthesis of chiral phthalides by efficient reductive cyclization of 2-acylarylcarboxylates under aqueous transfer hydrogenation conditions
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A new diamine ligand for asymmetric transfer hydrogenation (ATH) was discovered. The reductive cyclization of 2-acylarylcarboxylates was found to proceed highly stereoselective by the new Ru complex-catalyzed ATH and subsequent In situ lactonization under aqueous conditions. It enables efficient access to a wide variety of 3-substituted phthalides In enantiomerically pure form.
- Zhang, Bo,Xu, Ming-Hua,Lin, Guo-Qiang
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supporting information; experimental part
p. 4712 - 4715
(2009/12/08)
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- DIBENZOCYCLOHEPTENE COMPOUND
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The present invention discloses a dibenzocycloheptene compound represented by the formula (I): ???wherein R1: hydrogen atom, halogen atom, etc., R2: hydrogen atom, halogen atom, etc., A: 5-membered or 6-membered heteroaromatic ring group containing 1 to 3 hetero atom(s) selected from the group consisting of nitrogen atom, oxygen atom and sulfur atom, and the heteroaromatic ring group, etc. may have halogen atom, nitrogen atom, etc. as substituent(s), B: formula; -CH=CH-, formula; -CH2O-, etc., Y: C1-C10 alkylene group which may have halogen atom, etc. as substituent(s), etc., Z: carboxyl group which may be protected, etc., m: an integer of 1 to 4, n: an integer of 1 to 3, ???------ represents a single bond or a double bond, or a pharmaceutically acceptable salt thereof and a medical composition containing the same as an effective ingredient which has leukotriene C4 antagonistic action and leukotriene E4 antagonistic action in addition to potent leukotriene D4 antagonistic action, and useful as antiasthmatic agent, antiallergic agent and anti-inflammatory agent.
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- The imidazo[2,1-a]isoindole system. A new skeletal basis for antiplasmodial compounds
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The in vitro antiplasmodial activity of some dihydrostilbenamides, phtalazinones, imidazo[2,1-a]isoindole and pyrimido[2,1-a]isoindole derivatives related to the natural dihydrostilbenoid isonotholaenic acid is reported. The evaluation was performed on cultures of F32 strain of Plasmodium falciparum and potent representative compounds were also evaluated in the ferriprotoporphyrin IX biomineralization inhibition test (FBIT). Compounds having the imidazo[2,1-a]isoindole skeleton were the most active and one compound of this group resulted to be as potent as chloroquine, but acting through a mechanism different that of the inhibition of heme biomineralization.
- Del Olmo, Esther,Armas, Marlon Garcia,Ybarra, Ma. Ines,Lopez, Jose Luis,Oporto, Patricia,Gimenez, Alberto,Deharo, Eric,San Feliciano, Arturo
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p. 2769 - 2772
(2007/10/03)
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- Fused pyridine derivatives
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The present provides a condensed pyridine compound (I) represented by the following formula: (wherein, R2represents ring A represents benzene ring, pyridine ring, thiophene ring or furan ring; and B represents its pharmaceutically acceptable salt or hydrates thereof, which is a clinically useful medicament having a serotonin antagonism, in particular, that for treating, ameliorating or preventing spastic paralysis or central muscle relaxants for ameliorating myotonia.
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