One pot Click chemistry: A three component reaction for the synthesis of 2-mercaptobenzimidazole linked coumarinyl triazoles as anti-tubercular agents.

Abstract:

:2-Propargylthiobenzimidazole 1, 4-bromomethyl coumarins/1-aza-coumarins 2/3 and sodium azide have been reacted in one pot under Click chemistry conditions to give exclusively 1,4-disubstituted triazoles 5a-n. Anti-tubercular assays against M. tuberculosis (H37Rv) coupled with in silico molecular docking studies indicated that dimethyl substituents 5c and 5d showed promising activity with higher C-score values.

journal_name

Bioorg Med Chem Lett

authors

Anand A,Kulkarni MV,Joshi SD,Dixit SR

doi

10.1016/j.bmcl.2016.08.045

subject

Has Abstract

pub_date

2016-10-01 00:00:00

pages

4709-4713

issue

19

eissn

0960-894X

issn

1464-3405

pii

S0960-894X(16)30866-6

journal_volume

26

pub_type

杂志文章
  • Discovery and characterization of potent and selective 4-oxo-4-(5-(5-phenyl-1,2,4-oxadiazol-3-yl)indolin-1-yl)butanoic acids as S1P₁ agonists.

    abstract::S1P(1) receptor driven lymphopenia has proven utility in the treatment of an array of autoimmune disease states. As a part of our efforts to develop potent and selective S1P(1) receptor agonists, we have identified a novel chemical series of 4-oxo-4-(5-(5-phenyl-1,2,4-oxadiazol-3-yl)indolin-1-yl)butanoic acid S1P(1) r...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2011.05.110

    authors: Buzard D,Han S,Thoresen L,Moody J,Lopez L,Kawasaki A,Schrader T,Sage C,Gao Y,Edwards J,Barden J,Thatte J,Fu L,Solomon M,Liu L,Al-Shamma H,Gatlin J,Le M,Xing C,Espinola S,Jones RM

    更新日期:2011-10-01 00:00:00

  • An atom economic synthesis and antitubercular evaluation of novel spiro-cyclohexanones.

    abstract::The 1,3-dipolar cycloaddition of azomethine ylides derived from acenaphthenequinone and alpha-amino acids viz. sarcosine, phenylglycine, 1,3-thiazolane-4-carboxylic acid and proline to a series of 2,6-bis[(E)-arylmethylidene]cyclohexanones afforded novel spiro-heterocycles chemo-, regio- and stereoselectively in quant...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2009.05.018

    authors: Ranjith Kumar R,Perumal S,Manju SC,Bhatt P,Yogeeswari P,Sriram D

    更新日期:2009-07-01 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

  • Thymidine and thymidine-5'-O-monophosphate analogues as inhibitors of Mycobacterium tuberculosis thymidylate kinase.

    abstract::The affinity of a series of 2', 3'- and 5-modified thymidine analogues for Mycobacterium tuberculosis thymidine monophosphate kinase (TMPKmt) was evaluated. The affinities of several non-phosphorylated analogues are in the same order of magnitude as those of their phosphorylated congeners. In view of drug delivery pro...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(03)00643-7

    authors: Vanheusden V,Van Rompaey P,Munier-Lehmann H,Pochet S,Herdewijn P,Van Calenbergh S

    更新日期:2003-09-15 00:00:00

  • Synthesis and immunological activity of an oligosaccharide-conjugate as a vaccine candidate against Group A Streptococcus.

    abstract::The synthesis and immunogenicity of a tetanus toxoid (TT)-conjugate of the hexasaccharide portion of the cell-wall polysaccharide (CWPS) of the Group A Streptococcus (GAS) is described. The synthesis relies on the reaction of an allyl glycoside of the hexasaccharide with cysteamine, followed by the reaction of the res...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2013.09.042

    authors: Auzanneau FI,Borrelli S,Pinto BM

    更新日期:2013-11-15 00:00:00

  • Chroman-3-amides as potent Rho kinase inhibitors.

    abstract::Inhibition of Rho kinase (ROCK) is an attractive strategy for the treatment of diseases such as hypertension, glaucoma, and cancer. Here we report chroman-3-amides as highly potent ROCK inhibitors with sufficient kinase selectivity, excellent cell activity, good microsomal stability, and desirable pharmacokinetic prop...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2008.10.080

    authors: Chen YT,Bannister TD,Weiser A,Griffin E,Lin L,Ruiz C,Cameron MD,Schürer S,Duckett D,Schröter T,LoGrasso P,Feng Y

    更新日期:2008-12-15 00:00:00

  • Synthesis and biological activity of pyridopyridazin-6-one p38α MAP kinase inhibitors. Part 2.

    abstract::This manuscript concludes the Structure Activity Relationship (SAR) on the pyridazinone scaffold and identifies a compound with subnanomolar p38α activity and 24h coverage in the rat arthritis efficacy model. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2012.07.035

    authors: Tynebor RM,Chen MH,Natarajan SR,O'Neill EA,Thompson JE,Fitzgerald CE,O'Keefe SJ,Doherty JB

    更新日期:2012-09-15 00:00:00

  • Synthesis and biological evaluation of 99mTc, Re-monoamine-monoamide conjugated to 2-(4-aminophenyl)benzothiazole as potential probes for beta-amyloid plaques in the brain.

    abstract::The benzothiazole aniline (BTA) conjugated with monoamine-monoamide (MAMA) was synthesized and then labeled with (99m)Tc. Its corresponding rhenium analogue was synthesized, and the fluorescent staining was performed in brain sections of both Tg mouse and Alzheimer's disease (AD) patient. The fluorescent rhenium compl...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2007.12.071

    authors: Chen X,Yu P,Zhang L,Liu B

    更新日期:2008-02-15 00:00:00

  • Discovery of non-peptidergic MrgX1 and MrgX2 receptor agonists and exploration of an initial SAR using solid-phase synthesis.

    abstract::A class of small molecules displaying comparable activities with peptide ligands BAM22 and corticostatin-14 at both the human and rhesus monkey MrgX1 and MrgX2 receptors, respectively, was discovered. A comparative study to compare solid-phase and solution-phase chemistries for the efficient synthesis of the active cl...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2009.01.085

    authors: Malik L,Kelly NM,Ma JN,Currier EA,Burstein ES,Olsson R

    更新日期:2009-03-15 00:00:00

  • A chemically stable fluorescent marker of the ureter.

    abstract::Surgical methods guided by exogenous fluorescent markers have the potential to define tissue types in real time. Small molecule dyes with efficient and selective renal clearance could enable visualization of the ureter during surgical procedures involving the abdomen and pelvis. These studies report the design and syn...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2018.02.040

    authors: Cha J,Nani RR,Luciano MP,Kline G,Broch A,Kim K,Namgoong JM,Kulkarni RA,Meier JL,Kim P,Schnermann MJ

    更新日期:2018-09-01 00:00:00

  • Aminocyclohexylsulfonamides: discovery of metabolically stable alpha(1a/1d)-selective adrenergic receptor antagonists for the treatment of benign prostatic hyperplasia/lower urinary tract symptoms (BPH/LUTS).

    abstract::Benign prostatic hyperplasia/lower urinary tract symptoms (BPH/LUTS) can be effectively treated by alpha(1) adrenergic receptor antagonists, but these drugs also produce side effects that are related to their subtype non-selective nature. To overcome this limitation, it was hypothesized that an alpha(1a/1d) subtype-se...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2007.09.051

    authors: Chiu G,Li S,Cai H,Connolly PJ,Peng S,Stauber K,Pulito V,Liu J,Middleton SA

    更新日期:2007-11-15 00:00:00

  • Discovery, synthesis, and structure-activity studies of tetrazole based growth hormone secretagogues.

    abstract::A novel class of Growth Hormone Secretagogues (GHS), based on a tetrazole template, has been discovered. In vitro SAR and in vivo potency within this new class of GHS are described. The tetrazole 9q exhibits good oral bioavailability in rats and dogs as well as efficacy following an oral 10 mg/kg dose in dogs. Solutio...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2007.07.099

    authors: Hernández AS,Cheng PT,Musial CM,Swartz SG,George RJ,Grover G,Slusarchyk D,Seethala RK,Smith M,Dickinson K,Giupponi L,Longhi DA,Flynn N,Murphy BJ,Gordon DA,Biller SA,Robl JA,Tino JA

    更新日期:2007-11-01 00:00:00

  • Design, synthesis and enzymatic evaluation of 3-O-substituted aryl β-D-galactopyranosides as inhibitors of Trypanosoma cruzi trans-sialidase.

    abstract::The trans-sialidase of Trypanosoma cruzi (TcTS) is a surface enzyme that modifies the parasite glycocalyx covering it with sialic acid. This process is essential to adhesion and invasion mechanisms in life cycle of the protozoan in the human host, making TcTS a very attractive molecular target for drug design. Using t...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2014.07.088

    authors: Silva BL,S Filho JD,Andrade P,Carvalho I,Alves RJ

    更新日期:2014-09-15 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

  • Synthesis and cytotoxic activities of 2-substituted (25R)-spirostan-1,4,6-triene-3-ones via ring-opening/elimination and 'click' strategy.

    abstract::To develop more effective antitumor steroidal drugs, we synthesized a library including twenty-two novel cytotoxic 2-alkyloxyl substituted (25R)-spirostan-1,4,6-triene-3-ones and corresponding 1,2,3-triazoles through an abnormal monoepoxide ring-opening/elimination and 'click' reactions. After the cytotoxic evaluation...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2015.06.028

    authors: Lu XF,Yang Z,Huang NY,He HB,Deng WQ,Zou K

    更新日期:2015-09-01 00:00:00

  • Synthesis of substituted benzimidazolyl curcumin mimics and their anticancer activity.

    abstract::A novel curcumin mimic library (14a-14h and 15a-15h) possessing variously substituted benzimidazole groups was synthesized through the aldol reaction of (E)-4-(4-hydroxy-3-methoxyphenyl)but-3-en-2-one (7) or (E)-4-(3-hydroxy-4-methoxyphenyl)but-3-en-2-one (13) with diversely substituted benzimidazolyl-2-carbaldehyde (...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2011.12.074

    authors: Woo HB,Eom YW,Park KS,Ham J,Ahn CM,Lee S

    更新日期:2012-01-15 00:00:00

  • Polyether ionophores-promising bioactive molecules for cancer therapy.

    abstract::The natural polyether ionophore antibiotics might be important chemotherapeutic agents for the treatment of cancer. In this article, the pharmacology and anticancer activity of the polyether ionophores undergoing pre-clinical evaluation are reviewed. Most of polyether ionophores have shown potent activity against the ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章,评审

    doi:10.1016/j.bmcl.2012.09.046

    authors: Huczyński A

    更新日期:2012-12-01 00:00:00

  • Synthesis and investigations into the anticancer and antibacterial activity studies of β-carboline chalcones and their bromide salts.

    abstract::A series of sixteen β-carbolines, bearing chalcone moiety at C-1 position, were prepared from easily accessible 1-acetyl-β-carboline and various aldehydes under basic conditions followed by N2-alkylation using different alkyl bromides. The prepared compounds were evaluated for in vitro cytotoxicity against a panel of ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2018.03.033

    authors: Venkataramana Reddy PO,Hridhay M,Nikhil K,Khan S,Jha PN,Shah K,Kumar D

    更新日期:2018-05-01 00:00:00

  • Non-peptidic phenyl-based thrombin inhibitors: exploring structural requirements of the S1 specificity pocket with amidines.

    abstract::We expand the structural requirements and structure-activity relationship of a novel class of non-peptidic aryl-based thrombin inhibitors through exploration of the S1 specificity pocket of thrombin using flexible and constrained amidines. The most active compound of this class is 11 with Ki = 69 nM, which is ca. 15-f...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(99)00616-2

    authors: Lu T,Tomczuk B,Bone R,Murphy L,Salemme FR,Soll RM

    更新日期:2000-01-03 00:00:00

  • Study on structure-activity relationship of vitamin K derivatives: Conversion of the naphthoquinone part into another aromatic ring and evaluation of their neuronal differentiation-inducing activity.

    abstract::We synthesized novel vitamin K derivatives by converting the naphthoquinone group to benzene derivatives and benzoquinone. We evaluated their neuronal differentiation activities to investigate the effect of the quinone moiety on this process. We observed that the 1,4-quinone as well as the side chain part play importa...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2020.127059

    authors: Yoshimura H,Hirota Y,Soda S,Okazeri M,Takagi Y,Takeuchi A,Tode C,Kamao M,Osakabe N,Suhara Y

    更新日期:2020-04-15 00:00:00

  • Synthesis and structure-activity relationships of 7-(2-aminoalkyl)morpholinoquinolones as anti-Helicobacter pylori agents.

    abstract::A series of the titled compounds was synthesized and tested for anti-Helicobacter pylori activities. We discovered Y-34867 having the most potent activity against Helicobacter pylori among the quinolones tested along with high photostability. Furthermore, Y-34867 showed an excellent therapeutic effect in the experimen...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(98)00390-4

    authors: Sakurai N,Sano M,Hirayama F,Kuroda T,Uemori S,Moriguchi A,Yamamoto K,Ikeda Y,Kawakita T

    更新日期:1998-08-18 00:00:00

  • Design, synthesis, biological evaluation and molecular modeling of dihydropyrazole sulfonamide derivatives as potential COX-1/COX-2 inhibitors.

    abstract::Novel dihydropyrazole sulfonamide derivatives (30-56) were designed, synthesized, and evaluated for their biological activities as COX-1 and COX-2 inhibitors. In vitro biological evaluation against three human tumor cell lines revealed that most target compounds showed antiproliferative activities. Among the compounds...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2015.03.022

    authors: Chen Z,Wang ZC,Yan XQ,Wang PF,Lu XY,Chen LW,Zhu HL,Zhang HW

    更新日期:2015-05-01 00:00:00

  • Conjugation of spermine enhances cellular uptake of the stapled peptide-based inhibitors of p53-Mdm2 interaction.

    abstract::We report the first synthesis of the C-terminally spermine-conjugated stapled peptide-based inhibitors of the p53-Mdm2 interaction. Subsequent biological, biophysical and cellular uptake assays with the spermine-conjugated stapled peptides revealed that spermine conjugation minimally affects biological activity while ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2011.10.009

    authors: Muppidi A,Li X,Chen J,Lin Q

    更新日期:2011-12-15 00:00:00

  • Design, synthesis and biological activity evaluation of novel 4-((1-cyclopropyl-3-(tetrahydro-2H-pyran-4-yl)-1H-pyrazol-4-yl) oxy) pyridine-2-yl) amino derivatives as potent transforming growth factor-β (TGF-β) type I receptor inhibitors.

    abstract::TGF-β type I receptor (also known as activin-like kinase 5 or ALK5) plays a critical role in the progression of fibrotic diseases and tumor invasiveness and metastasis, as well. The development of small inhibitors targeting ALK5 has been validated as a potential therapeutic strategy for fibrotic diseases and cancer. H...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2020.127339

    authors: Tan B,Zhang X,Quan X,Zheng G,Li X,Zhao L,Li W,Li B

    更新日期:2020-08-15 00:00:00

  • Theoretical elucidation on structure-antioxidant activity relationships for indolinonic hydroxylamines.

    abstract::Indolinonic hydroxylamines (IH), representing a new type of antioxidants, are comparative to alpha-tocopherol to protect lipids from oxidation. To elucidate the structure-activity relationship for IH, B3LYP/6-31G(d, p) method was employed to calculate the O-H bond dissociation enthalpy (BDE), a theoretical parameter t...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(01)00724-7

    authors: Zhang HY,Wang LF

    更新日期:2002-01-21 00:00:00

  • Combinatorial search of substituted beta-cyclodextrins for phosphatase-like activity.

    abstract::Thirteen per-6-akylamino-6-deoxy-beta-cyclodextrin libraries (beta-CD libraries) were generated by a solution-phase combinatorial synthesis starting from per-6-iodo-6-deoxy-beta-CD and different combinations of eleven individual amine nucleophiles. Certain libraries showed the ability to hydrolyzep-nitrophenyl phospha...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(99)00468-0

    authors: Yu J,Zhao Y,Holterman MJ,Venton DL

    更新日期:1999-09-20 00:00:00

  • Biotin labelling of amines by polymer-assisted solution-phase synthesis.

    abstract::An efficient and simple polymer-assisted approach has been developed to biotinylate multifunctional compounds bearing an amino functionality. Biotin was immobilized on aminomethylated polystyrene via the Kenner safety catch linker, activated and subsequently transferred to the amino function of the target compounds ch...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(01)00296-7

    authors: Golisade A,Herforth C,Wieking K,Kunick C,Link A

    更新日期:2001-07-09 00:00:00

  • Discovery of phenyl acetamides as potent and selective GPR119 agonists.

    abstract::The paper describes the SAR/SPR studies that led to the discovery of phenoxy cyclopropyl phenyl acetamide derivatives as potent and selective GPR119 agonists. Based on a cis cyclopropane scaffold discovered previously, phenyl acetamides such as compound 17 were found to have excellent GPR119 potency and improved physi...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2017.01.091

    authors: Zhu C,Wang L,Zhu Y,Guo ZZ,Liu P,Hu Z,Szewczyk JW,Kang L,Chicchi G,Ehrhardt A,Woods A,Seo T,Woods M,van Heek M,Dingley KH,Pang J,Salituro GM,Powell J,Terebetski JL,Hornak V,Campeau LC,Orr RK,Ujjainwalla F,Mil

    更新日期:2017-03-01 00:00:00

  • Enzyme inhibition potency enhancement by active site metal chelating and hydrogen bonding induced conformation-restricted cyclopropanecarbonyl derivatives.

    abstract::Two cyclopropanecarbonyl derivatives were independently found to be 15 and 14 times more potent than the corresponding isopropylcarbonyl analogues as inhibitors of 4-hydroxyphenylpyruvate dioxygenase and dihydroorotate dehydrogenase, respectively. A thorough examination of the co-crystal structures of available enzyme...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2006.08.125

    authors: Kuo PY,Shie TL,Chen YS,Lai JT,Yang DY

    更新日期:2006-12-01 00:00:00

  • Novel, potent and orally bioavailable indolizidinone-derived inhibitors of the hepatitis C virus NS3 protease.

    abstract::A novel, potent, and orally bioavailable class of product-like inhibitors of the HCV NS3 protease was discovered by constraining the P2-P3 amide bond and the P3 hydrocarbon substituent to the protease-bound conformation. This preorganization was accomplished by incorporation of the P2-P3 amide into a six-membered ring...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2011.11.107

    authors: Clarke MO,Byun D,Chen X,Doerffler E,Leavitt SA,Sheng XC,Yang CY,Kim CU

    更新日期:2012-01-15 00:00:00