Synthesis of natural product-like polyprenylated phenols and quinones: Evaluation of their neuroprotective activities.

Abstract:

:Twenty-seven natural product-like polyprenylated phenols and quinones were synthesized and their neuroprotective activity was tested using human monoamine oxidase B (MAO-B) and SH-SY5Y cells. Eight compounds inhibited MAO-B (IC50 values < 25 μM) and the inhibition mode and molecular docking of two (8c and 16c) were investigated. Compounds inhibiting MAO-B activity were additionally tested for their ability to protect SH-SY5Y cells from peroxide injury. Three derivatives (3c, 8c and 16c) exhibited both MAO-B inhibitory and neuroprotective activity. A structure activity-relationship study showed that a phenolic hydroxyl group and a longer side chain are important for both activities.

journal_name

Bioorg Med Chem

authors

Kamauchi H,Oda T,Horiuchi K,Takao K,Sugita Y

doi

10.1016/j.bmc.2019.115156

subject

Has Abstract

pub_date

2020-01-01 00:00:00

pages

115156

issue

1

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(19)31230-1

journal_volume

28

pub_type

杂志文章
  • A new peptidyl fluorescent chemosensors for the selective detection of mercury ions based on tetrapeptide.

    abstract::A novel peptidyl chemosensor (PySO2-His-Gly-Gly-Lys(PySO2)-NH2, 1) was synthesized by incorporation of two pyrene (Py) fluorophores into the tetrapeptide using sulfonamide group. Compound 1 exhibited selective fluorescence response towards Hg(II) over the other metal ions in aqueous buffered solutions. Furthermore, 1 ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2013.09.058

    authors: Thirupathi P,Lee KH

    更新日期:2013-12-15 00:00:00

  • Responsive Mn(II) complexes for potential applications in diagnostic Magnetic Resonance Imaging.

    abstract::The investigation of new Mn(II)-based MRI/Molecular Imaging probes responsive to the enzyme tyrosinase for potential diagnostic applications is herein described. The expression of the enzyme tyrosinase, an oxidoreductase, is up-regulated in melanoma cancer cells. Three novel ligands (L(1), L(2) and L(3)) were designed...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2010.07.064

    authors: Rolla GA,Tei L,Fekete M,Arena F,Gianolio E,Botta M

    更新日期:2011-02-01 00:00:00

  • Synthesis and in vivo evaluation of [O-methyl-11C] N-[3,5-dichloro-2-(methoxy)phenyl]-4-(methoxy)-3-(1-piperazinyl)benzenesulfonamide as an imaging probe for 5-HT6 receptors.

    abstract::The serotonin receptor 6 (5-HT(6)) is implicated in the pathophysiology of cognitive diseases, schizophrenia, anxiety and obesity and in vivo studies of this receptor would be of value for studying the pathophysiology of these disorders. Therefore, N-[3,5-dichloro-2-(methoxy)phenyl]-4-(methoxy)-3-(1-piperazinyl)benzen...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2011.06.090

    authors: Liu F,Majo VJ,Prabhakaran J,Milak MS,John Mann J,Parsey RV,Kumar JS

    更新日期:2011-09-01 00:00:00

  • Synthesis of 6-N-(benzothiazol-2-yl)deoxyadenosine and its exciton-coupled circular dichroism.

    abstract::6-N-(Benzothiazol-2-yl)deoxyadenosine (A(BT)) was synthesized and incorporated into DNAs. Although, the multipoint benzothiazole (BT) modification of oligodeoxynucleotides reduced the stability of duplexes with their complementary strands, it induced the strong exciton coupling between BT moieties. The circular dichro...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2009.12.009

    authors: Masaki Y,Ohkubo A,Seio K,Sekine M

    更新日期:2010-01-15 00:00:00

  • Purinergic receptor P2X₇: a novel target for anti-inflammatory therapy.

    abstract::Purinergic receptors, also known as purinoceptors, are ligand gated membrane ion channels involved in many cellular functions. Among all identified purinergic receptors, P2X₇ subform is unique since it induces the caspase activity, cytokine secretion, and apoptosis. The distribution of P2X₇ receptors, and the need of ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.bmc.2013.10.054

    authors: Mehta N,Kaur M,Singh M,Chand S,Vyas B,Silakari P,Bahia MS,Silakari O

    更新日期:2014-01-01 00:00:00

  • Mechanism-based inhibitors of serine proteases with high selectivity through optimization of S' subsite binding.

    abstract::A series of mechanism-based inhibitors designed to interact with the S' subsites of serine proteases was synthesized and their inhibitory activity toward the closely-related serine proteases human neutrophil elastase (HNE) and proteinase 3 (PR 3) was investigated. The compounds were found to be time-dependent inhibito...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2009.04.011

    authors: Li Y,Dou D,He G,Lushington GH,Groutas WC

    更新日期:2009-05-15 00:00:00

  • Optimization and determination of the absolute configuration of a series of potent inhibitors of human papillomavirus type-11 E1-E2 protein-protein interaction: a combined medicinal chemistry, NMR and computational chemistry approach.

    abstract::We have previously reported the discovery and initial SAR optimization of the first series of inhibitors of the human papillomavirus type-11 (HPV11) E1-E2 protein-protein interaction. These inhibitors featured an indandione system spiro-fused onto an all syn substituted tetrahydrofuran ring. In this paper, we report n...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2007.01.036

    authors: Goudreau N,Cameron DR,Déziel R,Haché B,Jakalian A,Malenfant E,Naud J,Ogilvie WW,O'meara J,White PW,Yoakim C

    更新日期:2007-04-01 00:00:00

  • Structure-affinity relationships and pharmacological characterization of new alkyl-resorcinol cannabinoid receptor ligands: Identification of a dual cannabinoid receptor/TRPA1 channel agonist.

    abstract::In our ongoing program aimed at deeply investigating the endocannabinoid system (ES), a set of new alkyl-resorcinol derivatives was prepared focusing on the nature and the importance of the carboxamide functionality. Binding studies on CB1 and CB2 receptors, monoacylglycerol lipase (MAGL) and fatty acid amide hydrolas...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2014.07.006

    authors: Brizzi A,Aiello F,Marini P,Cascio MG,Corelli F,Brizzi V,De Petrocellis L,Ligresti A,Luongo L,Lamponi S,Maione S,Pertwee RG,Di Marzo V

    更新日期:2014-09-01 00:00:00

  • 2-(2-Bromophenyl)-formononetin and 2-heptyl-formononetin are PPARγ partial agonists and reduce lipid accumulation in 3T3-L1 adipocytes.

    abstract::Isoflavones are bioactive compounds that have been shown to decrease lipid accumulation in vitro. However, the knowledge of the isoflavone formononetin is limited. The aim of the study was to assess the effects of formononetin and its two synthetic analogues, 2-(2-bromophenyl)-formononetin and 2-heptyl-formononetin, o...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2014.08.037

    authors: Andersen C,Kotowska D,Tortzen CG,Kristiansen K,Nielsen J,Petersen RK

    更新日期:2014-11-01 00:00:00

  • New synthesis of (+/-)-alpha-CMBHC and its confirmation as a metabolite of alpha-tocopherol (vitamin E).

    abstract::There is currently interest in the metabolism of the various compounds which make up the vitamin E family, especially with regards to the possible use of vitamin E metabolites as markers of oxidative stress and adequate vitamin E supply. A number of vitamin E metabolites have been described to date and we have recentl...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(01)00010-4

    authors: Pope SA,Burtin GE,Clayton PT,Madge DJ,Muller DP

    更新日期:2001-05-01 00:00:00

  • An efficient substitution reaction for the preparation of thyroid hormone analogues.

    abstract::The substitution of the sterically hindered carbon of the potent thyroid hormone agonist, GC-1, was effected by a reaction based on the solvolysis of the benzylic hydroxyl group. The reaction was found to proceed in high yield with a variety of nucleophiles including alcohols, thiols, allyl silanes and electron-rich a...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(98)00085-6

    authors: Yoshihara HA,Chiellini G,Mitchison TJ,Scanlan TS

    更新日期:1998-08-01 00:00:00

  • Electronic effects of para-substitution on acetophenones in the reaction of rat liver 3alpha-hydroxysteroid dehydrogenase.

    abstract::Stereoselective reductive metabolism of various p-substituted acetophenone derivatives was studied using isolated rat liver 3alpha-hydroxysteroid dehydrogenase (3alpha-HSD). Kinetic experiments were performed and analyzed by measuring the products by HPLC using a chiral column. The results demonstrated that the presen...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2007.10.096

    authors: Uwai K,Konno N,Yasuta Y,Takeshita M

    更新日期:2008-02-01 00:00:00

  • N-(3-Acyloxy-2-benzylpropyl)-N'-(4-hydroxy-3-methoxybenzyl) thiourea derivatives as potent vanilloid receptor agonists and analgesics.

    abstract::A series of N-(3-acyloxy-2-benzylpropyl)-N'-(4-hydroxy-3-methoxybenzyl) thiourea derivatives were investigated as vanilloid receptor ligands in an effort to discover a novel class of analgesics. The proposed pharmacophore model of resiniferatoxin. which includes the C20 homovanillic moiety, the C3-carbonyl and the ort...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(00)00216-9

    authors: Lee J,Lee J,Kim J,Kim SY,Chun MW,Cho H,Hwang SW,Oh U,Park YH,Marquez VE,Beheshti M,Szabo T,Blumberg PM

    更新日期:2001-01-01 00:00:00

  • Elucidation of the topography of the thapsigargin binding site in the sarco-endoplasmic calcium ATPase.

    abstract::Removal of each of the acyl groups of thapsigargin at O-3, O-8 and O-10 significant reduces the affinity of the inhibitors to the SERCA1a pump. Replacement of the acyl groups at O-3 and O-10 with flexible residues could be performed with only a minor decrease of the affinity, whereas introduction of voluminous stiff r...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2010.06.032

    authors: Skytte DM,Møller JV,Liu H,Nielsen HØ,Svenningsen LE,Jensen CM,Olsen CE,Christensen SB

    更新日期:2010-08-01 00:00:00

  • Synthesis and evaluation of verticipyrone analogues as mitochondrial complex I inhibitors.

    abstract::Verticipyrone has recently been isolated from the culture broth of Verticillium sp. and shown to inhibit NADH fumarate reductase, as well as NADH oxidoreductase (complex I) of the mitochondrial electron transport chain. In order to assess the structural elements in verticipyrone essential for complex I inhibitor, 15 s...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2010.03.070

    authors: Leiris SJ,Khdour OM,Segerman ZJ,Tsosie KS,Chapuis JC,Hecht SM

    更新日期:2010-05-15 00:00:00

  • Synthesis of 11C-labelled (R)-OHDMI and CFMME and their evaluation as candidate radioligands for imaging central norepinephrine transporters with PET.

    abstract::(R)-1-(10,11-Dihydro-dibenzo[b,f]azepin-5-yl)-3-methylamino-propan-2-ol ((R)-OHDMI) and (S,S)-1-cyclopentyl-2-(5-fluoro-2-methoxy-phenyl)-1-morpholin-2-yl-ethanol (CFMME) were synthesized and found to be potent inhibitors of norepinephrine reuptake. Each was labelled efficiently in its methyl group with carbon-11 (t(1...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2006.10.065

    authors: Schou M,Pike VW,Sóvágó J,Gulyás B,Gallagher PT,Dobson DR,Walter MW,Rudyk H,Farde L,Halldin C

    更新日期:2007-01-15 00:00:00

  • Anti-tumor activity of the farnesyl-protein transferase inhibitors arteminolides, isolated from Artemisa.

    abstract::Members of the Artemisia genus are important medicinal plants found throughout the world. Arteminolides A-D (1-4), isolated from the aerial parts of Artemisia, have an inhibitory activity on farnesyl-protein transferase (FPTase; EC 2.5.1.29) in in vitro assay. This study was carried out with the purpose of validating ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2003.08.008

    authors: Lee SH,Lee MY,Kang HM,Han DC,Son KH,Yang DC,Sung ND,Lee CW,Kim HM,Kwon BM

    更新日期:2003-10-15 00:00:00

  • Synthesis and biological evaluations of A-ring isomers of 26,26,26,27,27,27-hexafluoro-1,25-dihydroxyvitamin D3.

    abstract::The activated vitamin D3 derivative 26,27-F6-1alpha,25(OH)2D3 (2a), its three A-ring diastereomers (2b, 2c, 2d), and 5,6-trans isomer (2e) were prepared. Two analogues (2b, 2c) of these isomers were synthesized by a palladium catalyzed coupling reaction using vinyl bromide 5 and enynes (6a, 6b), which were derived fro...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(00)00142-5

    authors: Ikeda M,Takahashi K,Dan A,Koyama K,Kubota K,Tanaka T,Hayashi M

    更新日期:2000-08-01 00:00:00

  • Thionation of segetalins A and B, cyclic peptides with estrogen-like activity from seeds of Vaccaria segetalis.

    abstract::Thionation of estrogen-like active cyclic peptides, segetalins A (1) and B (2), with Lawesson's reagent provided each two thiosegetalins; thiosegetalin A1 [Gly-1-psi(CS-NH)-Val-2; Trp-5-psi (CS-NH)-Ala-6]segetalin A, thiosegetalin A2 [Gly-1-psi(CS-NH)-Val-2; Ala-6-psi(CS-NH)-Gly-1]segetalin A, thiosegetalin B1 [Gly-1-...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(97)00001-1

    authors: Morita H,Yun YS,Takeya K,Itokawa H,Shirota O

    更新日期:1997-03-01 00:00:00

  • Synthesis of quinolinomorphinan-4-ol derivatives as δ opioid receptor agonists.

    abstract::The previously reported morphinan derivative SN-28 showed high selectivity and agonist activity for the δ opioid receptor. In the course of examining the structure-activity relationship of SN-28 derivatives, the derivatives with the 4-hydroxy group (SN-24, 26, 27) showed higher selectivities for the δ receptor over th...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2011.11.047

    authors: Ida Y,Nemoto T,Hirayama S,Fujii H,Osa Y,Imai M,Nakamura T,Kanemasa T,Kato A,Nagase H

    更新日期:2012-01-15 00:00:00

  • Synthesis and evaluation of [14C]-labelled and fluorescent-tagged paclitaxel derivatives as new biological probes.

    abstract::Our present report deals with the preparation of hitherto unreported 7-([carbonyl-14C]-acetyl)paclitaxel 4 and two new bioactive 7-substituted fluorescent taxoids (FITC 9 and rhodamine 11), as well as evaluation towards their applications as biological probes. The results in this report demonstrate that (a) the new pa...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(98)00158-8

    authors: Rao CS,Chu JJ,Liu RS,Lai YK

    更新日期:1998-11-01 00:00:00

  • Substituted 1,2,3,4-tetrahydroquinolin-6-yloxypropanes as beta3-adrenergic receptor agonists: design, synthesis, biological evaluation and pharmacophore modeling.

    abstract::In search of potent beta(3)-adrenergic receptor agonists, a series of novel substituted 1,2,3,4-tetrahydroquinolin-6-yloxypropanes has been synthesized and evaluated for their beta(3)-adrenergic receptor agonistic activity (ranging from -17.73% to 90.64% inhibition at 10 microM) using well established Human SK-N-MC ne...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2008.11.030

    authors: Shakya N,Roy KK,Saxena AK

    更新日期:2009-01-15 00:00:00

  • Synthesis and structure-activity relationships of benzophenone-bearing diketopiperazine-type anti-microtubule agents.

    abstract::KPU-105 (4), a potent anti-microtubule agent that contains a benzophenone was derived from the diketopiperazine-type vascular disrupting agent (VDA) plinabulin 3, which displays colchicine-like tubulin depolymerization activity. To develop derivatives with more potent anti-microtubule and cytotoxic activities, we furt...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2012.05.059

    authors: Yamazaki Y,Sumikura M,Masuda Y,Hayashi Y,Yasui H,Kiso Y,Chinen T,Usui T,Yakushiji F,Potts B,Neuteboom S,Palladino M,Lloyd GK,Hayashi Y

    更新日期:2012-07-15 00:00:00

  • Exploring new Probenecid-based carbonic anhydrase inhibitors: Synthesis, biological evaluation and docking studies.

    abstract::Novel Probenecid-based amide derivatives, incorporating different natural amino acids, were synthesized and assayed to test their effect on the human carbonic anhydrase (hCA, EC 4.2.1.1) transmembrane isoforms hCA IX and XII over the ubiquitous isoforms hCA I and II. Most of them presented a complete loss of hCA II in...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2015.07.066

    authors: Mollica A,Costante R,Akdemir A,Carradori S,Stefanucci A,Macedonio G,Ceruso M,Supuran CT

    更新日期:2015-09-01 00:00:00

  • Structural insights into the hot spot amino acid residues of mushroom tyrosinase for the bindings of thujaplicins.

    abstract::Tyrosinase inhibitors are important agents for cosmetic products. We examined here the inhibitory effects of three isomers of thujaplicins (α, β and γ) on mushroom tyrosinase and analyzed their binding modes using a homology model from the crystal structure of Streptomyces castaneoglobisporus tyrosinase (PDB ID: 1wx2)...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2010.08.056

    authors: Takahashi S,Kamiya T,Saeki K,Nezu T,Takeuchi S,Takasawa R,Sunaga S,Yoshimori A,Ebizuka S,Abe T,Tanuma S

    更新日期:2010-11-15 00:00:00

  • Search for new pharmacophores for antimalarial activity. Part II: synthesis and antimalarial activity of new 6-ureido-4-anilinoquinazolines.

    abstract::Synthesis of new 6-ureido-4-anilinoquinazolines have been accomplished and their in vitro antimalarial activity against chloroquine-sensitive P. falciparum have been examined. Out of 64 compounds evaluated, the IC(50) of 16 compounds which have displayed MIC of 0.25 microg/mL were also recorded. One of the compounds (...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2008.11.005

    authors: Madapa S,Tusi Z,Mishra A,Srivastava K,Pandey SK,Tripathi R,Puri SK,Batra S

    更新日期:2009-01-01 00:00:00

  • A concise approach to 1,11-didechloro-6-methyl-4'-O-demethyl rebeccamycin and its binding to human serum albumin: fluorescence spectroscopy and molecular modeling method.

    abstract::1,11-Didechloro-6-methyl-4'-O-demethyl rebeccamycin (JDC-108), a rebeccamycin analog possessing potent anti-tumor activities, was prepared via a concise one-pot strategy in good yield. The interaction between JDC-108 and human serum albumin (HSA) was studied by spectroscopic methods including fluorescence spectroscopy...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2008.07.017

    authors: Cui F,Qin L,Zhang G,Liu X,Yao X,Lei B

    更新日期:2008-08-15 00:00:00

  • 4,4'-Dihydroxy-trans-stilbene, a resveratrol analogue, exhibited enhanced antioxidant activity and cytotoxicity.

    abstract::Resveratrol (3,5,4'-trans-trihydroxystibene) is a natural phytoalexin present in grapes and red wine, which possesses a variety of biological activities including antioxidant activity. In order to find more active antioxidant with resveratrol as the lead compound we synthesized 4,4'-dihydroxy-trans-stilbene (4,4'-DHS)...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2009.02.014

    authors: Fan GJ,Liu XD,Qian YP,Shang YJ,Li XZ,Dai F,Fang JG,Jin XL,Zhou B

    更新日期:2009-03-15 00:00:00

  • Anthraquinone derivatives induce G2/M cell cycle arrest and apoptosis in NTUB1 cells.

    abstract::Thirteen anthraquinone derivatives 5-17 including two 3-(3-alkylaminopropoxy)-9,10-anthraquinone (NHA) derivatives 5 and 6, and 11 1-hydroxy-3-(3-alkylaminopropoxy)-9,10-anthraquinone (MHA) derivatives 7-17 were synthesized, evaluated for cytotoxicities against two cancer cell lines, and assayed the generation of reac...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2011.07.021

    authors: Tu HY,Huang AM,Teng CH,Hour TC,Yang SC,Pu YS,Lin CN

    更新日期:2011-09-15 00:00:00

  • 1,2,3,4-tetrahydroisoquinoline derivatives: a new class of 5-HT1A receptor ligands.

    abstract::Three series of new N-substituted 1,2,3,4-tetrahydroisoquinolines with 2-, 3-, and 4-membered alkyl chains (a, b, and c, respectively) were synthesized, and the effect of some structural modifications on their 5-HT1A receptor affinities and functional properties was discussed. It was found that the volume of the termi...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(98)00238-7

    authors: Mokrosz MJ,Bojarski AJ,Duszyńska B,Tatarczyńska E,Kłodzińska A,Dereń-Wesołek A,Charakchieva-Minol S,Chojnacka-Wójcik E

    更新日期:1999-02-01 00:00:00