Dicarboxylic acid esters as transdermal permeation enhancers: effects of chain number and geometric isomers.

Abstract:

:A series of transdermal permeation enhancers based on dicarboxylic acid esters was studied. Single-chain amphiphiles were markedly more effective than the double-chain ones. Monododecyl maleate, that is a cis derivative, was a more potent enhancer than its trans isomer, while the activity of succinates strongly depended on the donor vehicle. No difference between diastereoisomeric tartaric and meso-tartaric acid derivatives was found.

journal_name

Bioorg Med Chem Lett

authors

Novotný M,Hrabálek A,Janůsová B,Novotný J,Vávrová K

doi

10.1016/j.bmcl.2008.11.083

subject

Has Abstract

pub_date

2009-01-15 00:00:00

pages

344-7

issue

2

eissn

0960-894X

issn

1464-3405

pii

S0960-894X(08)01467-4

journal_volume

19

pub_type

杂志文章
  • 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

  • Discovery of imidazo[1,2-a]pyrazine-based Aurora kinase inhibitors.

    abstract::The synthesis and structure-activity relationships (SAR) of novel, potent imidazo[1,2-a]pyrazine-based Aurora kinase inhibitors are described. The X-ray crystal structure of imidazo[1,2-a]pyrazine Aurora inhibitor 1j is disclosed. Compound 10i was identified as lead compound with a promising overall profile. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2010.07.008

    authors: Belanger DB,Curran PJ,Hruza A,Voigt J,Meng Z,Mandal AK,Siddiqui MA,Basso AD,Gray K

    更新日期:2010-09-01 00:00:00

  • Calcitonin gene-related peptide (CGRP) receptor antagonists: pyridine as a replacement for a core amide group.

    abstract::In our continuing efforts to identify CGRP receptor antagonists that can be dosed orally for the treatment of migraine headache, we have investigated a pyridine bioisosteric replacement of a polar amide portion of a previous lead compound, BMS-694153. Pyridine derivatives were discovered and their SAR was studied. Som...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2012.02.065

    authors: Luo G,Chen L,Civiello R,Pin SS,Xu C,Kostich W,Kelley M,Conway CM,Macor JE,Dubowchik GM

    更新日期:2012-04-15 00:00:00

  • Sulfamoyl benzamides as novel CB2 cannabinoid receptor ligands.

    abstract::Sulfamoyl benzamides were identified as a novel series of cannabinoid receptor ligands. Starting from a screening hit 8 that had modest affinity for the cannabinoid CB(2) receptor, a parallel synthesis approach and initial SAR are described, leading to compound 27 with 120-fold functional selectivity for the CB(2) rec...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2008.04.006

    authors: Worm K,Zhou QJ,Saeui CT,Green RC,Cassel JA,Stabley GJ,DeHaven RN,Conway-James N,LaBuda CJ,Koblish M,Little PJ,Dolle RE

    更新日期:2008-05-01 00:00:00

  • Potent and selective CC-chemokine receptor-2 (CCR2) antagonists as a potential treatment for asthma.

    abstract::A number of compounds bearing a quaternary ammonium moiety were found to be antagonists with nanomolar binding affinity for the chemokine receptor-2. The structure-activity relationships in the series are described herein along with some detailed characterization of the interesting compounds. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2007.01.115

    authors: Lagu B,Gerchak C,Pan M,Hou C,Singer M,Malaviya R,Matheis M,Olini G,Cavender D,Wachter M

    更新日期:2007-08-01 00:00:00

  • 1,2,3-Thiadiazole thioacetanilides as a novel class of potent HIV-1 non-nucleoside reverse transcriptase inhibitors.

    abstract::A novel series of 1,2,3-thiadiazole thioacetanilide (TTA) derivatives have been designed, synthesized and evaluated for its anti-HIV activities in MT-4 cells. Some derivatives proved to be highly effective in inhibiting HIV-1 replication at nanomolar concentrations. Among them, 2-[4-(2,4-dichlorophenyl)-1,2,3-thiadiaz...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2008.09.055

    authors: Zhan P,Liu X,Cao Y,Wang Y,Pannecouque C,De Clercq E

    更新日期:2008-10-15 00:00:00

  • Enediynes: Exploration of microbial genomics to discover new anticancer drug leads.

    abstract::The enediyne natural products have been explored for their phenomenal cytotoxicity. The development of enediynes into anticancer drugs has been successfully achieved through the utilization of polymer- and antibody-drug conjugates (ADCs) as drug delivery systems. An increasing inventory of enediynes would benefit curr...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章,评审

    doi:10.1016/j.bmcl.2014.11.019

    authors: Shen B,Hindra,Yan X,Huang T,Ge H,Yang D,Teng Q,Rudolf JD,Lohman JR

    更新日期:2015-01-01 00:00:00

  • N-substituted azaindoles as potent inhibitors of Cdc7 kinase.

    abstract::Cdc7 kinase is responsible for the initiation and regulation of DNA replication and has been proposed as a target for cancer therapy. We have identified a class of Cdc7 inhibitors based on a substituted indole core. Synthesis of focused indole and azaindole analogs yielded potent and selective 5-azaindole Cdc7 inhibit...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2013.02.007

    authors: Bryan MC,Falsey JR,Frohn M,Reichelt A,Yao G,Bartberger MD,Bailis JM,Zalameda L,Miguel TS,Doherty EM,Allen JG

    更新日期:2013-04-01 00:00:00

  • Anti-tubercular agents. Part IV: Synthesis and antimycobacterial evaluation of nitroheterocyclic-based 1,2,4-benzothiadiazines.

    abstract::In continuation of our earlier work on benzothiadiazines, we have prepared a series of nitrofuran, nitrothiophene and arylfuran coupled benzothiadiazines and evaluated them for antimycobacterial and antibacterial activities. One of the compounds 2f has shown good in vitro antimycobacterial activity. All the synthesize...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2007.07.027

    authors: Kamal A,Ahmed SK,Reddy KS,Khan MN,Shetty RV,Siddhardha B,Murthy US,Khan IA,Kumar M,Sharma S,Ram AB

    更新日期:2007-10-01 00:00:00

  • 4-Phenyl-4-[1H-imidazol-2-yl]-piperidine derivatives, a novel class of selective delta-opioid agonists.

    abstract::A novel series of 4-phenyl-4-[1H-imidazol-2-yl]-piperidine derivatives has been prepared and their synthesis described herein. In vitro affinities for delta-, mu-, and kappa-opioid receptors, as well as the functional activity in the [(35)S]GTPgammaS assay are reported. The most potent and selective delta-opioid agoni...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2005.09.025

    authors: Trabanco AA,Pullan S,Alonso JM,Alvarez RM,Andrés JI,Boeckx I,Fernández J,Gómez A,Iturrino L,Janssens FE,Leenaerts JE,De Lucas AI,Matesanz E,Meert T,Steckler T

    更新日期:2006-01-01 00:00:00

  • A novel approach toward bacteriochlorophylls-e and f.

    abstract::Methyl bacteriopheophorbide-f was prepared from methyl bacteriopheophorbide-d with retention of the 3(1)-chirality. The transformation of the methyl to the formyl group at the 7-position of the chlorin moiety will provide an alternative route for the synthesis of bacteriochlorophylls-e and f. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(99)00258-9

    authors: Tamiaki H,Omoda M,Kubo M

    更新日期:1999-06-21 00:00:00

  • Combined tachykinin receptor antagonist: synthesis and stereochemical structure-activity relationships of novel morpholine analogues.

    abstract::We report herein the synthesis and stereochemical structure-activity relationships of novel morpholine analogues 12 and 13 with regards to NK1, NK2 and NK3 tachykinin receptor binding affinity. An essential requirement for more potent binding affinities was controlled by absolute configuration. (S,R)-12 and (S,R)-13 e...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(00)00324-3

    authors: Nishi T,Ishibashi K,Takemoto T,Nakajima K,Fukazawa T,Iio Y,Itoh K,Mukaiyama O,Yamaguchi T

    更新日期:2000-08-07 00:00:00

  • Enhanced estrogen receptor beta (ERβ) selectivity of fluorinated carborane-containing ER modulators.

    abstract::We previously showed that fluorination of the carborane-containing selective estrogen receptor modulator (SERM) BE360 altered the agonist/antagonist activity balance and the estrogen receptor (ER) α/β subtype selectivity. Here, we designed and synthesized a series of fluorinated carboranyl phenols as candidate ERβ-sel...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2013.10.067

    authors: Ohta K,Ogawa T,Kaise A,Endo Y

    更新日期:2013-12-15 00:00:00

  • New coumarin-benzotriazole based hybrid molecules as inhibitors of acetylcholinesterase and amyloid aggregation.

    abstract::A novel series of triazole tethered coumarin-benzotriazole hybrids based on donepezil skeleton has been designed and synthesized as multifunctional agents for the treatment of Alzheimer's disease (AD). Among the synthesized compounds 13b showed most potent acetylcholinesterase (AChE) inhibition (IC50 = 0.059 μΜ) with ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2020.127477

    authors: Singh A,Sharma S,Arora S,Attri S,Kaur P,Kaur Gulati H,Bhagat K,Kumar N,Singh H,Vir Singh J,Mohinder Singh Bedi P

    更新日期:2020-10-15 00:00:00

  • Imidazopyridine CB2 agonists: optimization of CB2/CB1 selectivity and implications for in vivo analgesic efficacy.

    abstract::A new series of imidazopyridine CB2 agonists is described. Structural optimization improved CB2/CB1 selectivity in this series and conferred physical properties that facilitated high in vivo exposure, both centrally and peripherally. Administration of a highly selective CB2 agonist in a rat model of analgesia was inef...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2011.02.082

    authors: Trotter BW,Nanda KK,Burgey CS,Potteiger CM,Deng JZ,Green AI,Hartnett JC,Kett NR,Wu Z,Henze DA,Della Penna K,Desai R,Leitl MD,Lemaire W,White RB,Yeh S,Urban MO,Kane SA,Hartman GD,Bilodeau MT

    更新日期:2011-04-15 00:00:00

  • Structure-activity relationships of adenosine A3 receptor ligands: new potential therapy for the treatment of glaucoma.

    abstract::Structure-activity relationships (SAR) of fused 1,2,4-triazolo[1,5-c ]pyrimidine were performed. Various substituents were introduced into the heterocyclic ring to improve the potency of adenosine A(3) receptor binding affinity and A(3)-selectivity against other subtypes. Potent and selective A(3) receptor antagonists...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2004.04.099

    authors: Okamura T,Kurogi Y,Hashimoto K,Sato S,Nishikawa H,Kiryu K,Nagao Y

    更新日期:2004-07-16 00:00:00

  • Compound instability in dimethyl sulphoxide, case studies with 5-aminopyrimidines and the implications for compound storage and screening.

    abstract::The oxidation reactions of 5-aminopyrimidine derivatives in dimethyl sulphoxide (DMSO) were studied. The DMSO solutions of the studied compounds became deeply coloured within a few hours or days. The oxidation products can undergo further condensation reactions with the starting pyrimidines to yield bipyrimidines and/...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2012.08.065

    authors: Procházková E,Jansa P,Březinová A,Cechová L,Mertlíková-Kaiserová H,Holý A,Dračínský M

    更新日期:2012-10-15 00:00:00

  • Juglone, isolated from Juglans mandshurica Maxim, induces apoptosis via down-regulation of AR expression in human prostate cancer LNCaP cells.

    abstract::Juglone is a natural compound which has been isolated from Juglans mandshurica Maxim. Recent studies have shown that juglone had various pharmacological effects such as anti-viral, anti-bacterial and anti-cancer. However, its anti-cancer activity on human prostate cancer LNCaP cell has not been examined. Thus, the cur...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 信件

    doi:10.1016/j.bmcl.2013.04.007

    authors: Xu H,Yu X,Qu S,Sui D

    更新日期:2013-06-15 00:00:00

  • Targeting tyrosine kinase: Development of acridone - pyrrole - oxindole hybrids against human breast cancer.

    abstract::Based on the molecular modelling studies, a rational modification of the lead molecule was made to develop highly potent compounds showing anti-cancer activity against human breast cancer cell lines MCF 7, MDA-MB-468 and T-47D. The most potent compounds have Log P and total polar surface area 4.4-5.4 and 59.8 Å, respe...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2018.11.021

    authors: Kaur M,Singh P

    更新日期:2019-01-01 00:00:00

  • Folate pro-drug of cystamine as an enhanced treatment for nephropathic cystinosis.

    abstract::Nephropathic cystinosis is a rare autosomal recessive disease characterised by raised intracellular levels of the amino acid, cystine. If untreated, the disease, progressively deteriorates towards end stage renal disease (ESRD) at the end of the first decade. The disease is caused by a defect in the lysosomal transpor...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2011.02.048

    authors: Omran Z,Kay G,Hector EE,Knott RM,Cairns D

    更新日期:2011-04-15 00:00:00

  • Synthesis of [18F]SU11248, a new potential PET tracer for imaging cancer tyrosine kinase.

    abstract::N-[2-(Diethylamino)ethyl]-5-[(Z)-(5-[18F]fluoro-2-oxo-1,2-dihydro-3H-indol-3-ylidene)methyl]-2,4-dimethyl-1H-pyrrole-3-carboxamide, a new potential positron emission tomography tracer for imaging cancer tyrosine kinase, has been prepared by the nucleophilic substitution of the nitro-precursor N-[2-(diethylamino)ethyl]...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2005.06.038

    authors: Wang JQ,Miller KD,Sledge GW,Zheng QH

    更新日期:2005-10-01 00:00:00

  • Structure-based design, synthesis and biological evaluation of a novel series of isoquinolone and pyrazolo[4,3-c]pyridine inhibitors of fascin 1 as potential anti-metastatic agents.

    abstract::Fascin is an actin binding and bundling protein that is not expressed in normal epithelial tissues but overexpressed in a variety of invasive epithelial tumors. It has a critical role in cancer cell metastasis by promoting cell migration and invasion. Here we report the crystal structures of fascin in complex with a s...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2019.01.035

    authors: Francis S,Croft D,Schüttelkopf AW,Parry C,Pugliese A,Cameron K,Claydon S,Drysdale M,Gardner C,Gohlke A,Goodwin G,Gray CH,Konczal J,McDonald L,Mezna M,Pannifer A,Paul NR,Machesky L,McKinnon H,Bower J

    更新日期:2019-04-15 00:00:00

  • Design, synthesis, and cytostatic activity of novel cyclic curcumin analogues.

    abstract::A series of novel cyclic analogues of curcumin were synthesized and analyzed for in vitro cytostatic activity. Condensation of 2-acetylcycloalkanones with a variety of aromatic aldehydes resulted in the formation of 2-arylidene-6-(3-arylacryoyl)-cycloalkanone derivatives. A number of these analogues were found to have...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2007.07.079

    authors: Youssef D,Nichols CE,Cameron TS,Balzarini J,De Clercq E,Jha A

    更新日期:2007-10-15 00:00:00

  • Total synthesis of mololipids: a new series of anti-HIV Moloka'iamine derivatives.

    abstract::A new family of bioactive bromotyrosine derivatives, termed mololipids, was recently isolated from a Hawaiian sponge, but could not be resolved into individual components by chromatography. To complete their structural characterization and better understand structure-activity relationships, the first pure samples of d...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(00)00543-6

    authors: Schoenfeld RC,Lumb JP,Fantini J,Ganem B

    更新日期:2000-12-04 00:00:00

  • Effects of alkyl parabens on plant pathogenic fungi.

    abstract::Alkyl parabens are used as antimicrobial preservatives in cosmetics, food, and pharmaceutical products. However, the mode of action of these chemicals has not been assessed thoroughly. In this study, we determined the effects of alkyl parabens on plant pathogenic fungi. All the fungi tested, were susceptible to parabe...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2015.02.049

    authors: Ito S,Yazawa S,Nakagawa Y,Sasaki Y,Yajima S

    更新日期:2015-04-15 00:00:00

  • Anti-inflammatory property of the urinary metabolites of nobiletin in mouse.

    abstract::Nobiletin, a major component of polymethoxyflavones in citrus fruits, has a broad spectrum of health beneficial properties including anti-inflammatory and anti-carcinogenic activities. The metabolite identification of nobiletin in mouse urine has concluded that it undergoes mono-demethylation (3'- and 4'-demethylnobil...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2007.06.096

    authors: Li S,Sang S,Pan MH,Lai CS,Lo CY,Yang CS,Ho CT

    更新日期:2007-09-15 00:00:00

  • Kinetic investigation of human 5-lipoxygenase with arachidonic acid.

    abstract::Human 5-lipoxygenase (5-LOX) is responsible for the formation of leukotriene (LT)A4, a pivotal intermediate in the biosynthesis of the leukotrienes, a family of proinflammatory lipid mediators. 5-LOX has thus gained attention as a potential drug target. However, details of the kinetic mechanism of 5-LOX are still obsc...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2016.06.025

    authors: Mittal M,Kumar RB,Balagunaseelan N,Hamberg M,Jegerschöld C,Rådmark O,Haeggström JZ,Rinaldo-Matthis A

    更新日期:2016-08-01 00:00:00

  • Novel fluoroquinolones: design, synthesis, and in vivo activity in mice against Mycobacterium tuberculosis H37Rv.

    abstract::Novel 6,8-difluoro-1-alkyl-5-amino-1,4-dihydro-4-oxo-7-{4-substituted piperazin-1-yl}-quinoline-3-carboxylic acids, with the substituents at 4th position of piperazine being -[2(pyridine-4-carbonyl) hydrazono]propyl and -2 [(pyrazine-2-carbonyl) amino] ethyl, were synthesized and evaluated in vivo against Mycobacteriu...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2005.02.037

    authors: Shindikar AV,Viswanathan CL

    更新日期:2005-04-01 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

  • Aspergillus candidus is a newly recognized source of sphaeropsidin A: Isolation, semi-synthetic derivatization and anticancer evaluation.

    abstract::This report details a search for alternative strains that produce the diterpenoid sphaeropsidin A (SphA) among A. candidus strains from the USDA Northern Regional Research Laboratories Culture Collection. We identified two strains that produced SphA using a limited set of test media. An initial scaled-up fermentation ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2017.11.001

    authors: Li Y,Scott R,Hooper AR,Bartholomeusz GA,Kornienko A,Bills GF

    更新日期:2017-12-15 00:00:00