- Synthesis and activity of a coumarin-based fluorescent probe for hydroxyl radical detection
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As a type of reactive oxygen species (ROS), hydroxyl radical (·OH) is closely associated with many kinds of diseases. The present study aimed to develo p a novel OH fluorescent probe based on coumarin, a new compound that has not been previously reported.
- Zhang, Bin,Xu, Lijing,Zhou, Yindi,Zhang, Weijian,Wang, Yuanhong,Zhu, Yu
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Read Online
- Dirigent proteins from cotton (Gossypium sp.) for the atropselective synthesis of gossypol
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Gossypol is a defense compound in cotton plants for protection against pests and pathogens. Gossypol biosynthesis involves the oxidative coupling of hemigossypol and results in two atropisomers owing to hindered rotation around the central binaphthyl bond
- Effenberger, Isabelle,Zhang, Bin,Li, Ling,Wang, Qiang,Liu, Yuxiu,Klaiber, Iris,Pfannstiel, Jens,Wang, Qingmin,Schaller, Andreas
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Read Online
- Regioselective oxidative dehydrogenation under nonenzymatic conditions: A synthetic route to gossypol
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A practical and scalable route was developed for the total synthesis of gossypol to allow for the construction of dozens of gossypol derivatives. tBuO2Ac was found to be a highly efficient oxidant for the polymerization of hemigossypol through a biosynthetic process under nonenzymatic conditions to give gossypol. Hemigossypol was synthesized on a gram scale by starting from commercially available carvacrol and dimethyl succinate and using a Stobbe condensation, an electrophilic cyclization, and the Michael addition of ortho-quinone methide as key steps. A practical route was developed for the total synthesis of racemic gossypol. tBuO2Ac was found to be a highly efficient oxidant for the polymerization of hemigossypol under nonenzymatic conditions to give gossypol. Hemigossypol was synthesized on a gram scale from commercially available carvacrol and dimethyl succinate. Copyright
- Li, Ling,Liu, Yuxiu,Wang, Qingmin
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Read Online
- An efficient synthesis of rearranged new biologically active benzimidazoles derived from 2-formyl carvacrol
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A new series of benzimidazole derivatives was synthesized by one-pot two-step reaction as a result of unexpected rearrangement during reaction of 2-formyl carvacrol and corresponding 2-phenylenediamines in DMF, by using Na2S2O5 as an oxidizing reagent. The newly synthesized compounds were characterized by 1H NMR, 13C NMR, FT-IR, mass spectroscopy techniques, and single-crystal X-ray crystallography. The docking studies of all nine compounds were carried out against the active site of the Plasmodium falciparum dihydroorotate dehydrogenase enzyme. To inspect their antimalarial, antimicrobial, and antioxidant activity, all the synthesized compounds were screened in vitro for their antimalarial activity against the malaria parasite Plasmodium falciparum strain and four bacterial as well as three fungal strains. The biological screening revealed that some synthesized compounds have very good antimalarial activity. The physicochemical properties were calculated for all the synthesized benzimidazoles and were found to be good oral bioavailability drugs as resolute by Lipinski's rule. Graphic abstract: [Figure not available: see fulltext.]
- Bhoi, Rahul T.,Rajput, Jamatsing D.,Bendre, Ratnamala S.
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p. 401 - 422
(2021/11/01)
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- Synthesis, characterizations, biological activities and docking studies of novel dihydroxy derivatives of natural phenolic monoterpenoids containing azomethine linkage
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Abstract: In the present work, we report the synthesis of six new azomethine linkage containing dihydroxy derivatives of carvacrol, thymol, and eugenol. All the synthesized derivatives have been characterized by spectroscopic techniques and their structures were confirmed by X-ray single crystallography. Synthesized derivatives were screened for anti-oxidant activity using DPPH radical scavenging assay, and anticancer activity by using SRB assay against pancreatic cancer with MIAPaCa-2 and colon cancer with HCT-15 cell lines. The molecular docking studies of all the synthesized derivatives were performed on cyclooxygenases (COX-2) protein enzyme. In the anti-oxidant test, the values of EC50 indicated that all the compounds show excellent anti-oxidant potency, and similarly the GI50 values in anticancer tests indicated that most of the compounds possess good anticancer efficacy. The overall docking score suggested that all the synthesized compounds exhibit good binding affinity towards cyclooxygenases (COX-2) protein enzyme.
- Rajput, Jamatsing D.,Bagul, Suresh D.,Hosamani, Amar A.,Patil, Manohar M.,Bendre, Ratnamala S.
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p. 5377 - 5393
(2017/09/23)
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- Synthesis, biological activities and molecular docking simulation of hydrazone scaffolds of carvacrol, thymol and eugenol
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In present work, we report the synthesis of 12 new hydrazones and sulfonyl hydrazones linkage containing carvacrol, thymol and eugenol derivatives by simple condensation reactions. Synthesized derivatives have been characterized by 1H NMR, 13C NMR, LC–MS, and X-ray single crystallography techniques, and these derivatives were screened for anticancer testing by using sulforhodamine B assay and anti-oxidant testing by using DPPH assay. Docking studies of all the derivatives against the active site of human heme oxygenase-1 indicated that interaction with the maximum site of the amino acid residue of human heme oxygenase-1 was crucial for anti-oxidant activity. The results show that all derivatives possess interesting biological activities.
- Rajput, Jamatsing D.,Bagul, Suresh D.,Bendre, Ratnamala S.
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p. 6601 - 6616
(2017/10/05)
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- Hemigossypol derivative, vergosin derivative, preparation of hemigossypol derivative and vergosin derivative and application to pesticides
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The invention relates to a hemigossypol derivative, a vergosin derivative, preparation of the hemigossypol derivative and the vergosin derivative and application to preventing plant viruses, killing bacteria and killing insects. Meaning of groups in the f
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Paragraph 0048-0052
(2018/02/04)
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- INK COMPOSITION, INKJET RECORDING METHOD, PRINTED MATTER, AND HIGH-MOLECULAR-WEIGHT POLYMERIZATION INITIATOR
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An ink composition contains (component A) a high-molecular-weight polymerization initiator having a weight-average molecular weight of equal to or greater than 1,000, (component B) a polymerizable compound, and (component C) a colorant, in which the component A has an acylphosphine oxide structure, and the acylphosphine oxide structure is linked to a main chain or a core of the component A on the side of an acyl group thereof.
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- Asymmetric induction via short-lived chiral enolates with a chiral C-O axis
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A novel method has been developed for the asymmetric cyclization of alkyl aryl ethers. The reactions were assumed to proceed via short-lived chiral enolate intermediates with a chiral C-O axis to give cyclic ethers with tetrasubstituted carbon in up to 99% ee. The half-life of racemization of the chiral enolate intermediate was roughly estimated to be ~1 s at -78 C.
- Yoshimura, Tomoyuki,Tomohara, Keisuke,Kawabata, Takeo
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supporting information
p. 7102 - 7105
(2013/06/27)
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- 7-alkyl-3-benzylcoumarins: A versatile scaffold for the development of potent and selective cannabinoid receptor agonists and antagonists
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A series of 7-alkyl-3-benzylcoumarins was designed, synthesized, and tested at cannabinoid CB1 and CB2 receptors in radioligand binding and cAMP accumulation studies. 7-Alkyl-3-benzylcoumarins were found to constitute a versatile scaffold for obtaining potent CB receptor ligands with high potency at either CB1 or CB2 and a broad spectrum of efficacies. Fine-tuning of compound properties was achieved by small modifications of the substitution pattern. The most potent compounds of the present series include 5-methoxy-3-(2-methylbenzyl)-7-pentyl-2H-chromen-2-one (19a, PSB-SB-1201), a selective CB1antagonist (Ki CB 1 0.022 μM), 5-methoxy-3-(2-methoxybenzyl)-7-pentyl-2H-chromen-2- one (21a, PSB-SB-1202), a dual CB1/CB2agonist (CB 1Ki 0.032 μM, EC50 0.056 μM; CB 2Ki 0.049 μM, EC50 0.014 μM), 5-hydroxy-3-(2-hydroxybenzyl)-7-(2-methyloct-2-yl)-2H-chromen-2-one (25b, PSB-SB-1203), a dual CB1/CB2 ligand that blocks CB 1 but activates CB2 receptors (CB1Ki 0.244 μM; CB2Ki 0.210 μM, EC50 0.054 μM), and 7-(1-butylcyclopentyl)-5-hydroxy-3-(2-hydroxybenzyl)-2H-chromen-2- one (27b, PSB-SB-1204), a selective CB2 receptor agonist (CB 1Ki 1.59 μM; CB2Ki 0.068 μM, EC50 0.048 μM).
- Rempel, Viktor,Volz, Nicole,Hinz, Sonja,Karcz, Tadeusz,Meliciani, Irene,Nieger, Martin,Wenzel, Wolfgang,Br?se, Stefan,Müller, Christa E.
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p. 7967 - 7977
(2012/11/07)
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- Radical and migratory insertion reaction mechanisms in Schiff base zirconium alkyls
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Four salicylaldimine derivatives H2L4-7 of 2,2′-diamino-6,6′-dimethylbiphenyl, where the CN bond is sterically protected by substituents on the phenol ring, form alkyls of zirconium, cis-α-[ZrL4-7(CH2Ph)2/
- Knight, Paul D.,Clarkson, Guy,Hammond, Max L.,Kimberley, Brian S.,Scott, Peter
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p. 5125 - 5144
(2007/10/03)
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- A New Preparative Route to Substituted Dibenzofurans by Benzannulation Reaction. An Application to the Synthesis of Cannabifuran
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A new regioselective pathway to substituted dibenzofuran derivatives is described here. According to this procedure substituted 1-acetoxy-3- alkoxycarbonyl dibenzofurans are obtained by treatment of 6-(2-methoxyaryl)-3- alkoxycarbonylhex-3-en-5-ynoic acids with acetic anhydride in the presence of sodium acetate. The latter acids are prepared from the easily available substituted o-iodo-anisoles by Sonogashira coupling with propargylic alcohol and Wittig reaction as the key steps. The described benzannulation reaction proceeds in regioselective fashion and a range of substituents are tolerated. Its synthetic utility is demonstrated by a new synthesis of cannabifuran, a naturally occurring dibenzofuran.
- Serra, Stefano,Fuganti, Claudio
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p. 2005 - 2008
(2007/10/03)
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The aromatic hydroxyaldehydes 3a-3g, 5a-Sf, 8, 10 can be prepared by the action of BCl3, BBr3 or trifluoromethanesulfonic acid, on the aryl formates 1a-1f, 4a-e, 7, 9 via Fries rearrangement. BBr3 is more effective than BCl3. The activating ability of BBr3 can be improved by addition of FeCl3. Rearrangements which are induced by trifluoromethanesulfonic acid can give rise to the formations of regioisomers, which might be different from the products formed when the reaction is performed with Lewis acids. The yields of the aldehydes are lowered by subsequent condensation reactions. This view was confirmed by the isolation of a condensation product, which was characterized as a dibenzo[a,j]xanthene derivative 6 by crystal structure analysis. For the Fries rearrangement of formyl groups a new mechanism is proposed. 2-Hydroxy-1-naphthaldehyde 5c can be obtained in good yield from formic acid, BBr3, and 2-naphthol.
- Ziegler, Georg,Haug, Erwin,Frey, Wolfgang,Kantlehner, Willi
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p. 1178 - 1187
(2007/10/03)
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- Cannabis. Part 28. A New Route to the Synthesis of Cannabifuran
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The total synthesis of the naturally occuring dibenzofuran cannabifuran (9-isopropyl-6-methyl-3-pentyldibenzofuran-1-ol) (25) is presented.In the key step, starting from 2,3-dimethoxy-p-toluic acid and 2-bromo-1,3-dimethoxy-5-pentylbenzene, the aryl-aryl
- Novak, Jiri,Salemink, Cornelis A.
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p. 2873 - 2878
(2007/10/02)
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- Naturally Occurring Dibenzofurans. Part 1. A Synthesis of Cannabifuran
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The synthesis of dibenzofurans from diphenyl ethers by non-phenolic oxidative coupling, u.v. irradiation, and by reaction with palladium(II) acetate has been investigated. 9-Isopropyl-6-methyl-3-pentyldibenzofuran-1-ol (cannabifuran) (35), a minor cannabi
- Sargent, Melvyn V.,Stransky, Peter O.
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p. 1605 - 1610
(2007/10/02)
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