Diamine preparation for synthesis of a water soluble Ni(II) salen complex.

Abstract:

:A reliable and efficient synthesis of a Ni(II) salen complex useful in probing nucleic acid structure is described and illustrates a general approach for constructing cis diamines suitable for assembly into N2O2 Schiff base complexes. Two equivalents of an aryllithium reacted with 1,4-dimethylpiperazine-2,3-dione to form the symmetric alpha-dione. This material was then converted to its dioxime and reduced by TiCl4/NaBH4 to yield the meso-diamine. Condensation of the diamine and salicyladehyde, coordination of nickel and final methylation generated the desired water soluble and redox active complex.

journal_name

Bioorg Med Chem Lett

authors

Shearer JM,Rokita SE

doi

10.1016/s0960-894x(99)00020-7

subject

Has Abstract

pub_date

1999-02-08 00:00:00

pages

501-4

issue

3

eissn

0960-894X

issn

1464-3405

pii

S0960894X99000207

journal_volume

9

pub_type

杂志文章
  • A facile synthesis, antibacterial activity of pulvinone and its derivatives.

    abstract::Pulvinone and several 3-fluoro-4-morpholino substituted pulvinone derivatives were synthesized in five steps from a common precursor, phenyl acetic acid. Most of synthetic morpholine substituted pulvinones showed inhibitory activity against Esherichia coli. For the first time, the inhibition of pulvinone and its deriv...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2012.11.090

    authors: Xu HW,Xu C,Fan ZQ,Zhao LJ,Liu HM

    更新日期:2013-02-01 00:00:00

  • Synthesis of doxorubicin-peptide conjugate with multidrug resistant tumor cell killing activity.

    abstract::Cell penetrating peptide TAT was introduced into doxorubicin structure. Synthesized doxorubicin-TAT conjugate showed different intracellular distribution pattern and cell killing activity from those of free doxorubicin. Unlike free doxorubicin, doxorubicin-TAT conjugate was highly permeable to drug-resistant cells and...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2005.07.087

    authors: Liang JF,Yang VC

    更新日期:2005-11-15 00:00:00

  • Discovery of 3-(2-aminoethyl)-5-(3-phenyl-propylidene)-thiazolidine-2,4-dione as a dual inhibitor of the Raf/MEK/ERK and the PI3K/Akt signaling pathways.

    abstract::A thiazolidine-2,4-dione derivative, 3-(2-aminoethyl)-5-(3-phenyl-propylidene)-thiazolidine-2,4-dione (2), was identified as a dual inhibitor of the Raf/MEK/ extracellular signal-regulated kinase (ERK) and the phosphatidylinositol 3-kinase (PI3K)/Akt signaling cascades. The discovered compound inhibited cell prolifera...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2010.06.030

    authors: Li Q,Wu J,Zheng H,Liu K,Guo TL,Liu Y,Eblen ST,Grant S,Zhang S

    更新日期:2010-08-01 00:00:00

  • 3,4-Dihydronaphthalen-1(2H)-ones: novel ligands for the benzodiazepine site of alpha5-containing GABAA receptors.

    abstract::A series of substituted 3,4-dihydronaphthalen-1(2H)-ones with high binding affinity for the benzodiazepine site of GABAA receptors containing the alpha5-subunit has been identified. These compounds have consistently higher binding affinity for the GABAA alpha5 receptor subtype over the other benzodiazepine-sensitive G...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2004.03.054

    authors: Szekeres HJ,Atack JR,Chambers MS,Cook SM,Macaulay AJ,Pillai GV,MacLeod AM

    更新日期:2004-06-07 00:00:00

  • New mannose derivatives: The tetrazole analogue of mannose-6-phosphate as angiogenesis inhibitor.

    abstract::Two novel compounds with mannose-derived structure, bearing a tetrazole (compound 3) and a sulfone group (compound 4) in terminal position, have been prepared from methyl α-d-mannopyranoside in reduced number of steps. The angiogenic activity of 3 and 4 has been screened using the chick chorioallantoic membrane (CAM) ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2015.11.059

    authors: Ionescu C,Sippelli S,Toupet L,Barragan-Montero V

    更新日期:2016-01-15 00:00:00

  • Pyrimido-oxazepine as a versatile template for the development of inhibitors of specific kinases.

    abstract::Pyrimido-oxazepine based sub-micromolar inhibitors (2-4) for Aurora and FLT-3 were designed and synthesized. These preliminary results supported the potential use of pyrimido-oxazepines as a versatile template for developing specific kinase inhibitors. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2005.08.098

    authors: Pan W,Liu H,Xu YJ,Chen X,Kim KH,Milligan DL,Columbus J,Hadari YR,Kussie P,Wong WC,Labelle M

    更新日期:2005-12-15 00:00:00

  • Synthesis and SAR development of novel P2X7 receptor antagonists for the treatment of pain: part 1.

    abstract::Structure-activity relationship (SAR) efforts around our initial lead compound 1 led to the identification of potent P2X(7) receptor antagonists with improved pharmacokinetic profiles. These compounds were potent and selective at the P2X(7) receptor in both human and rodent. Compound (entry 31) exhibited oral efficacy...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2011.04.034

    authors: Matasi JJ,Brumfield S,Tulshian D,Czarnecki M,Greenlee W,Garlisi CG,Qiu H,Devito K,Chen SC,Sun Y,Bertorelli R,Geiss W,Le VD,Martin GS,Vellekoop SA,Haber J,Allard ML

    更新日期:2011-06-15 00:00:00

  • Synthesis and biological evaluation of L- and D-configuration 1,3-dioxolane 5-azacytosine and 6-azathymine nucleosides.

    abstract::Novel L- and D-configuration dioxolane 5-azacytosine and 6-azathymine nucleosides have been synthesized and evaluated for biological activity. (-)-(2S,4S)-1-[2-(Hydroxymethyl)-1,3-dioxolan-4-yl]-5-azacytosine (6) showed significant activity against HBV, whereas the D-configuration analogue (14) has been found to exhib...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(00)00418-2

    authors: Luo MZ,Liu MC,Mozdziesz DE,Lin TS,Dutschman GE,Gullen EA,Cheng YC,Sartorelli AC

    更新日期:2000-09-18 00:00:00

  • Pre-microRNA binding aminoglycosides and antitumor drugs as inhibitors of Dicer catalyzed microRNA processing.

    abstract::Over-expressions of miRNAs are being increasingly linked with many diseases including different types of cancer. In this study, the role of some known small molecular therapeutics has been investigated for their ability to bind with the pre-miRNA target (hsa-mir-155) and thereby to interfere with the Dicer catalyzed m...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2011.12.103

    authors: Maiti M,Nauwelaerts K,Herdewijn P

    更新日期:2012-02-15 00:00:00

  • Structure-based design of isoindoline-1,3-diones and 2,3-dihydrophthalazine-1,4-diones as novel B-Raf inhibitors.

    abstract::Structure-guided design led to the discovery of novel chemical scaffolds for B-Raf inhibitors. Both type I and type II kinase inhibitors have been explored and lead compounds with good potency and excellent selectivity have been identified. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2011.10.012

    authors: Wang X,Salaski EJ,Berger DM,Powell D,Hu Y,Wojciechowicz D,Collins K,Frommer E

    更新日期:2011-12-01 00:00:00

  • Novel malonamide derivatives as potent kappa opioid receptor agonists.

    abstract::A novel series of malonamide derivatives was synthesized. These amides were shown to be potent and selective kappa opioid receptor agonists. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2007.01.053

    authors: Chu GH,Gu M,Cassel JA,Belanger S,Graczyk TM,DeHaven RN,Conway-James N,Koblish M,Little PJ,DeHaven-Hudkins DL,Dolle RE

    更新日期:2007-04-01 00:00:00

  • Carbonic anhydrase inhibitors: Selective inhibition of the extracellular, tumor-associated isoforms IX and XII over isozymes I and II with glycosyl-thioureido-sulfonamides.

    abstract::A series of glycosyl-thioureido sulfonamides incorporating glucosamine, galactosamine, and mannosamine tails, and sulfanilamide, halogenosulfanilamide, and metanilamide heads was synthesized. Many of the new compounds showed micromolar-submicromolar affinity for the inhibition of the cytosolic isoforms I and II of the...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2007.07.019

    authors: Smaine FZ,Winum JY,Montero JL,Regainia Z,Vullo D,Scozzafava A,Supuran CT

    更新日期:2007-09-15 00:00:00

  • Synthesis and in vitro evaluation of hydrazinyl phthalazines against malaria parasite, Plasmodium falciparum.

    abstract::In this report, we describe the synthesis of 1-(Phthalazin-4-yl)-hydrazine using bronsted acidic ionic liquids and demonstrate their ability to inhibit asexual stage development of human malaria parasite, Plasmodium falciparum. Through computational studies, we short-listed chemical scaffolds with potential binding af...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2016.05.049

    authors: Subramanian G,Babu Rajeev CP,Mohan CD,Sinha A,Chu TTT,Anusha S,Ximei H,Fuchs JE,Bender A,Rangappa KS,Chandramohanadas R,Basappa

    更新日期:2016-07-15 00:00:00

  • Preliminary in vivo evaluation of a novel 99mTc-labeled HYNIC-cys-annexin A5 as an apoptosis imaging agent.

    abstract::A novel cys-annexin A5 with a single cysteine-residue at its concave side has been developed by site-directed mutagenesis to allow conjugation through thiol-chemistry without affecting its apoptotic cell binding properties and was derivatized with HYNIC in a 1:1 stoichiometry. Similar to that of the 1st generation 99m...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2008.05.044

    authors: Fonge H,de Saint Hubert M,Vunckx K,Rattat D,Nuyts J,Bormans G,Ni Y,Reutelingsperger C,Verbruggen A

    更新日期:2008-07-01 00:00:00

  • Structure-activity relationship in two series of aminoalkyl substituted coumarin inhibitors of gyrase B.

    abstract::Two series of aminosubstituted coumarins were synthesised and evaluated in vitro as inhibitors of DNA gyrase and as potential antibacterials. Novel novobiocin-like coumarins, 4-(dialkylamino)methylcoumarins and 4-((2-alkylamino)ethoxy)coumarins, were discovered as gyrase B inhibitors with promising antibacterial activ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(99)00492-8

    authors: Laurin P,Ferroud D,Schio L,Klich M,Dupuis-Hamelin C,Mauvais P,Lassaigne P,Bonnefoy A,Musicki B

    更新日期:1999-10-04 00:00:00

  • Design, synthesis and biological evaluation of novel semicarbazone-selenochroman-4-ones hybrids as potent antifungal agents.

    abstract::A series of novel 2,3-dihydro-4H-1-benzoselenin-4-one (thio)semicarbazone derivatives were designed and synthesized by using molecular hybridization approach. All the target compounds were characterized by HRMS and NMR and evaluated in vitro antifungal activity against five pathogenic strains. In comparison with precu...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2019.126726

    authors: Xu H,Su X,Liu XQ,Zhang KP,Hou Z,Guo C

    更新日期:2019-12-01 00:00:00

  • Synthesis, fungicidal activity and SAR of 3,4-dichloroisothiazole-based cycloalkylsulfonamides.

    abstract::To develop more valuable and effective fungicide candidates, a novel series of 3,4-dichloroisothioxazole-based cycloalkylsulfonamides were synthesized and their structures were identified by 1H NMR, 13C NMR, MS and elemental analysis. Compound 3k was further confirmed by X-ray single crystal diffraction. The in vitro ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2019.03.047

    authors: Zhang Y,Wang M,Ahmed M,He L,Ji M,Qi Z,Li X

    更新日期:2019-06-01 00:00:00

  • Synthesis and the hepatoprotective activity of dibenzocyclooctadiene lignan derivatives.

    abstract::The halogenated and oxidized derivatives (1a-1e, 1a'-1c', 2a-2d, 2a'-2b', 3a-3e, 3' and 3a'-3b') of schizandrin (1), schizandrin B (2) and schisanhenol (3) were synthesized. The hepatoprotective effects of these dibenzocyclooctadiene lignan analogues against CCl4-induced injury were preliminarily evaluated. Most of th...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2014.02.020

    authors: He T,Wang QY,Shi JZ,Fan TY,Yan C,Huang LJ,Liu S,Hao XJ,Mu SZ

    更新日期:2014-04-01 00:00:00

  • Discovery of 2,6-difluorobenzyl ether series of phenyl ((R)-3-phenylpyrrolidin-3-yl)sulfones as surprisingly potent, selective and orally bioavailable RORγt inverse agonists.

    abstract::In an effort to discover oral inverse agonists of RORγt to treat inflammatory diseases, a new 2,6-difluorobenzyl ether series of cyclopentyl sulfones were found to be surprisingly more potent than the corresponding alcohol derivatives. When combined with a more optimized phenyl ((R)-3-phenylpyrrolidin-3-yl)sulfone tem...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2020.127441

    authors: Duan JJ,Jiang B,Lu Z,Stachura S,Weigelt CA,Sack JS,Khan J,Ruzanov M,Wu DR,Yarde M,Shen DR,Zhao Q,Salter-Cid LM,Carter PH,Murali Dhar TG

    更新日期:2020-10-01 00:00:00

  • Novologues containing a benzamide side chain manifest anti-proliferative activity against two breast cancer cell lines.

    abstract::Hsp90 represents a promising target for the development of both anti-cancer and neuroprotective agents. Structure-activity relationship studies on novobiocin and novobiocin analogues, led to the development of KU-32 and recently, KU-596, as lead compounds for the potential treatment of neurodegenerative diseases. Simi...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2014.05.020

    authors: Zhao H,Anyika M,Girgis A,Blagg BS

    更新日期:2014-08-01 00:00:00

  • Tetrahydroquinoline derivatives as opioid receptor antagonists.

    abstract::Opioid receptors play an important role in both behavioral and homeostatic functions. We herein report tetrahydroquinoline derivatives as opioid receptor antagonists. SAR studies led to the identification of the potent antagonist 2v, endowed with 1.58nM (K(i)) functional activity against the μ opioid receptor. DMPK da...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2010.12.010

    authors: Zhang C,Westaway SM,Speake JD,Bishop MJ,Goetz AS,Carballo LH,Hu M,Epperly AH

    更新日期:2011-01-15 00:00:00

  • Synthesis of pyrazole peptidomimetics and their inhibition against A549 lung cancer cells.

    abstract::A series of novel pyrazole peptidomimetics was synthesized from 3-aryl-1-arylmethyl-1H-pyrazole-5-carboxylic acid and amino acid ester. Structures of the compounds were characterized by means of IR, (1)H NMR and mass spectroscopy. Compounds 5e and 5k suppress effectively the growth of A549 lung cancer cells. Prelimina...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2012.09.032

    authors: Liu YR,Luo JZ,Duan PP,Shao J,Zhao BX,Miao JY

    更新日期:2012-11-15 00:00:00

  • Discovery of novel nonsteroidal glucocorticoid receptor modulators.

    abstract::A new class of selective nonsteroidal glucocorticoid receptor modulators typified by N-[3-[benzyl-(4-chloro-2-fluoro-benzyl)-amino]-2-methyl-phenyl]-methanesulfonamide 19 has been discovered. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2004.02.013

    authors: Link JT,Sorensen BK,Patel J,Emery M,Grynfarb M,Goos-Nilsson A

    更新日期:2004-05-03 00:00:00

  • Cluster analysis and two-dimensional quantitative structure-activity relationship (2D-QSAR) of Pseudomonas aeruginosa deacetylase LpxC inhibitors.

    abstract::Compounds from a wide variety of structural classes inhibit Pseudomonas aeruginosa deacetylase LpxC. However, a single unified understanding of the relationship between the structures and activities of these compounds still eludes the researchers. We report herein, the development of cluster analysis-based 2D-QSAR mod...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2006.07.041

    authors: Kadam RU,Roy N

    更新日期:2006-10-01 00:00:00

  • Synthesis and biological activity of macrocyclic taxane analogues.

    abstract::A series of paclitaxel analogues possessing a macrocyclic structure between the 7 and 10 positions has been prepared. These compounds possess in vitro activity against a paclitaxel resistant cell line and have in vivo activity comparable to paclitaxel. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2004.02.086

    authors: Tarrant JG,Cook D,Fairchild C,Kadow JF,Long BH,Rose WC,Vyas D

    更新日期:2004-05-17 00:00:00

  • Nociceptin/Orphanin FQ(1-13)NH2 analogues modified in the Phe1-Gly2 peptide bond.

    abstract::The synthesis and pharmacological activity of novel nociceptin/orphanin FQ (N/OFQ) analogues modified in the Phe(1)-Gly(2) peptide bond are reported. The aim of the present work was to elucidate the importance of this peptide bond for the N/OFQ receptor (NOP) interaction. Our study indicates that the first peptide bon...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(02)01004-1

    authors: Guerrini R,Rizzi D,Zucchini M,Tomatis R,Regoli D,Calo' G,Salvadori S

    更新日期:2003-02-10 00:00:00

  • Trifluoromethyl ketones as inhibitors of histone deacetylase.

    abstract::Trifluoromethyl ketones were found to be inhibitors of histone deacetylases (HDACs). Optimization of this series led to the identification of submicromolar inhibitors such as 20 that demonstrated antiproliferative effects against the HT1080 and MDA 435 cell lines. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(02)00754-0

    authors: Frey RR,Wada CK,Garland RB,Curtin ML,Michaelides MR,Li J,Pease LJ,Glaser KB,Marcotte PA,Bouska JJ,Murphy SS,Davidsen SK

    更新日期:2002-12-02 00:00:00

  • Evaluation of a series of bicyclic CXCR2 antagonists.

    abstract::The CXCR2 SAR of a series of bicyclic antagonists such as the 2-aminothiazolo[4,5-d]pyrimidine 3b was investigated by systematic variation of the fused pyrimidine-based heterocyclic cores. Replacement of the aminothiazole ring with a 2-thiazolone alternative led to a series of thiazolo[4,5-d]pyrimidine-2(3H)-one antag...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2007.11.039

    authors: Walters I,Austin C,Austin R,Bonnert R,Cage P,Christie M,Ebden M,Gardiner S,Grahames C,Hill S,Hunt F,Jewell R,Lewis S,Martin I,David Nicholls,David Robinson

    更新日期:2008-01-15 00:00:00

  • N-Alkyl-N-arylmethylpiperidin-4-amines: novel dual inhibitors of serotonin and norepinephrine reuptake.

    abstract::A series of N-alkyl-N-arylmethylpiperidin-4-amines have been prepared and are demonstrated to be inhibitors of both serotonin and norepinephrine reuptake. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2006.02.008

    authors: Boot JR,Boulet SL,Clark BP,Cases-Thomas MJ,Delhaye L,Diker K,Fairhurst J,Findlay J,Gallagher PT,Gilmore J,Harris JR,Masters JJ,Mitchell SN,Naik M,Simmonds RG,Smith SM,Richards SJ,Timms GH,Whatton MA,Wolfe CN,Wood

    更新日期:2006-05-15 00:00:00

  • Synthesis of novel benzothiazole amides: Evaluation of PPAR activity and anti-proliferative effects in paraganglioma, pancreatic and colorectal cancer cell lines.

    abstract::The reduced activation of PPARs has a positive impact on cancer cell growth and viability in multiple preclinical tumor models, suggesting a new therapeutic potential for PPAR antagonists. In the present study, the benzothiazole amides 2a-g were synthesized and their activities on PPARs were investigated. Transactivat...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2019.06.020

    authors: Ammazzalorso A,De Lellis L,Florio R,Laghezza A,De Filippis B,Fantacuzzi M,Giampietro L,Maccallini C,Tortorella P,Veschi S,Loiodice F,Cama A,Amoroso R

    更新日期:2019-08-15 00:00:00