An efficient synthesis of [1,3]dioxolo[4,5-g]thieno[3,4-b]quinolin-8(5H)-ones as novel thiazapodophyllotoxin analogues with potential anticancer activity.


:A catalyst-free synthesis of 6,9-dihydro-[1,3]dioxolo[4,5-g]thieno[3,4-b]quinolin-8(5H)-ones as novel analogues of podophyllotoxins was developed by a three-component reaction of aldehydes, ethyl 2,4-dioxotetrahydrothiophene-3-carboxylate and 3,4-(methylenedioxy)aniline. This methodology not only provides new chemical library for the screening of anticancer activity, but also features excellent isolated yields, short reaction time, simple work up procedure and little environmental impact.


Bioorg Med Chem Lett


Li T,Lu T,Yu C,Yao C




Has Abstract


2015-04-01 00:00:00














  • Synthesis and evaluation of 3-¹²³I-iodo-5-[2-(S)-3-pyrrolinylmethoxy]-pyridine (niodene) as a potential nicotinic α4β2 receptor imaging agent.

    abstract::Nicotinic acetylcholine receptors (nAChRs) are downregulated in disease conditions such as Alzheimer's and substance abuse. Presently, (123)I-5-IA-85380 is used in human studies and requires over 6h of scanning time, thus increases patient discomfort. We have designed and synthesized 3-iodo-5-[2-(S)-3-pyrrolinylmethox...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Pandey SK,Pan S,Kant R,Kuruvilla SA,Pan ML,Mukherjee J

    更新日期:2012-12-15 00:00:00

  • Investigation of 7-benzylidenenaltrexone derivatives as resistance reverser for chloroquine-resistant Plasmodium chabaudi.

    abstract::Derivatives of 7-benzylidenenaltrexone (BNTX), which was recently reported to be an effective chloroquine (CQ)-resistance reverser, were synthesized and evaluated for their CQ-resistance reversing activities. The synthesized derivatives showed CQ-resistance reversing effects. They also reacted with glutathione (GSH) b...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Miyata Y,Fujii H,Uenohara Y,Kobayashi S,Takeuchi T,Nagase H

    更新日期:2012-08-15 00:00:00

  • Synthesis of β-boswellic acid derivatives as cytotoxic and apoptotic agents.

    abstract::A series of β-boswellic acid derivatives were synthesized and evaluated for anticancer activity. One of the lead analog 4f displayed significant anticancer activity against a panel of cancer cells as well as substantially inhibited colony formation in HCT-116 cells. Furthermore, 4f was found to be a potent inducer of ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Kumar A,Qayum A,Sharma PR,Singh SK,Shah BA

    更新日期:2016-01-01 00:00:00

  • Potent hFPRL1 (ALXR) agonists as potential anti-inflammatory agents.

    abstract::We report the discovery of potent agonists for the human formyl-peptide-like 1 receptor (hFPRL1). These compounds did not act at a closely related receptor denoted human formyl peptide receptor (hFPR) up to 10 microM concentration. Recent studies have indicated that agonizing this receptor may promote resolution of in...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Bürli RW,Xu H,Zou X,Muller K,Golden J,Frohn M,Adlam M,Plant MH,Wong M,McElvain M,Regal K,Viswanadhan VN,Tagari P,Hungate R

    更新日期:2006-07-15 00:00:00

  • ATB0,+-targeted delivery of triptolide prodrugs for safer and more effective pancreatic cancer therapy.

    abstract::Triptolide (TP) is a diterpene epoxide component extracted from Tripterygium wilfordii and has been shown to possess an impressive anticancer effect. However, TP has not yet entered any clinic trials due to the severe adverse effects that resulted from the off-target absorption and distribution found in animal studies...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Lou D,Lou Z,Lin Y,Shangguan H,Lin Y,Luo Q,Zhang H,Lin G,Chen R,Kou L,Bao S

    更新日期:2020-12-17 00:00:00

  • Topical 'dual-soft' glucocorticoid receptor agonist for dermatology.

    abstract::Steroidal glucocorticoids (GR agonists) have been widely used for the topical treatment of skin disorders, including atopic dermatitis. They are a very effective therapy, but they are associated with both unwanted local effects in the skin (skin thinning/atrophy) and systemic side effects. These effects can limit the ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Dack KN,Johnson PS,Henriksson K,Eirefelt S,Carnerup MA,Stahlhut M,Ollerstam AK

    更新日期:2020-09-01 00:00:00

  • Structure-activity relationship studies of a bisbenzimidazole-based, Zn(2+)-dependent inhibitor of HCV NS3 serine protease.

    abstract::A survey of isosteric replacements of the phosphonoalanine side chain coupled with a process of conformational constraint of a bisbenzimidazole-based, Zn(2+)-dependent inhibitor of hepatitis C virus (HCV) NS3 serine protease resulted in the identification of novel series of active compounds with extended side chains. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Yeung KS,Meanwell NA,Qiu Z,Hernandez D,Zhang S,McPhee F,Weinheimer S,Clark JM,Janc JW

    更新日期:2001-09-03 00:00:00

  • Pterin-sulfa conjugates as dihydropteroate synthase inhibitors and antibacterial agents.

    abstract::The sulfonamide class of antibiotics has been in continuous use for over 70years. They are thought to act by directly inhibiting dihydropteroate synthase (DHPS), and also acting as prodrugs that sequester pterin pools by forming dead end pterin-sulfonamide conjugates. In this study, eight pterin-sulfonamide conjugates...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Zhao Y,Shadrick WR,Wallace MJ,Wu Y,Griffith EC,Qi J,Yun MK,White SW,Lee RE

    更新日期:2016-08-15 00:00:00

  • Benzimidazole derivatives protect against cytokine-induced apoptosis in pancreatic β-Cells.

    abstract::Apoptotic cell death is the cause of the loss of insulin-producing β-cells in all forms of diabetes mellitus. The identification of small molecules capable of protecting cytokine-induced apoptosis could form the basis of useful therapeutic interventions. Here in, we present the discovery and synthesis of new benzimida...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Zawawi NK,Rajput SA,Taha M,Ahmat N,Ismail NH,Abdullah N,Khan KM,Choudhary MI

    更新日期:2015-10-15 00:00:00

  • Synthesis and inhibitory activity of 4-alkynyl and 4-alkenylquinazolines: identification of new scaffolds for potent EGFR tyrosine kinase inhibitors.

    abstract::The present study identified several 4-alkynyl and 4-alkenylquinazolines that serve as novel and potent EGFR tyrosine kinase inhibitors. The IC(50) values of these compounds are in the nanomolar range. In addition, the 4-(4-phenylbut-1-yn/en-yl)quinazolines provided scaffolds for potent enzyme inhibition. Chiral discr...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Kitano Y,Suzuki T,Kawahara E,Yamazaki T

    更新日期:2007-11-01 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


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

    更新日期:2005-10-01 00:00:00

  • Elucidation of antimicrobial activity and mechanism of action by N-substituted carbazole derivatives.

    abstract::Compounds belonging to a carbazole series have been identified as potent fungal plasma membrane proton adenosine triphophatase (H+-ATPase) inhibitors with a broad spectrum of antifungal activity. The carbazole compounds inhibit the adenosine triphosphate (ATP) hydrolysis activity of the essential fungal H+-ATPase, the...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Clausen JD,Kjellerup L,Cohrt KO,Hansen JB,Dalby-Brown W,Winther AL

    更新日期:2017-10-01 00:00:00

  • Discovery of potent selective bioavailable phosphodiesterase 2 (PDE2) inhibitors active in an osteoarthritis pain model. Part II: optimization studies and demonstration of in vivo efficacy.

    abstract::Selective phosphodiesterase 2 (PDE2) inhibitors are shown to have efficacy in a rat model of osteoarthritis (OA) pain. We identified potent, selective PDE2 inhibitors by optimizing residual PDE2 activity in a series of phosphodiesterase 4 (PDE4) inhibitors, while minimizing PDE4 inhibitory activity. These newly design...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Plummer MS,Cornicelli J,Roark H,Skalitzky DJ,Stankovic CJ,Bove S,Pandit J,Goodman A,Hicks J,Shahripour A,Beidler D,Lu XK,Sanchez B,Whitehead C,Sarver R,Braden T,Gowan R,Shen XQ,Welch K,Ogden A,Sadagopan N,Baum H

    更新日期:2013-06-01 00:00:00

  • Discovery of liver selective non-steroidal glucocorticoid receptor antagonist as novel antidiabetic agents.

    abstract::Series of benzyl-phenoxybenzyl amino-phenyl acid derivatives (8a-q) are reported as non-steroidal GR antagonist. Compound 8g showed excellent h-GR binding and potent antagonistic activity (in vitro). The lead compound 8g exhibited significant oral antidiabetic and antihyperlipidemic effects (in vivo), along with liver...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Shah K,Patel D,Jadav P,Sheikh M,Sairam KV,Joharapurkar A,Jain MR,Bahekar R

    更新日期:2012-09-15 00:00:00

  • Syntheses and anti-inflammatory activity of azamollugin derivatives.

    abstract::Oxomollugin (2) is a degradation product of mollugin (1) and a potent inhibitor of NO-production including nuclear factor kappa B signals. In our endeavor to develop a potent anti-inflammatory compound, we synthesized several aza-derivatives of oxomollugin (2) and evaluated their NO-production inhibitory activity. Aza...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Nishino H,Nakajima Y,Kakubari Y,Asami N,Deguchi J,Nugroho AE,Hirasawa Y,Kaneda T,Kawasaki Y,Goda Y,Morita H

    更新日期:2016-01-15 00:00:00

  • Discovery of conformationally rigid 3-azabicyclo[3.1.0]hexane-derived dipeptidyl peptidase-IV inhibitors.

    abstract::The induction of conformationally restricted N-(aryl or heteroaryl)-3-azabicyclo[3.1.0]hexane derivatives at P(2) region of compounds of 2-cyanopyrrolidine class was explored to develop novel DPP-IV inhibitors. The synthesis, structure-activity relationship, and selectivity against related proteases are delineated. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Sattigeri JA,Andappan MM,Kishore K,Thangathirupathy S,Sundaram S,Singh S,Sharma S,Davis JA,Chugh A,Bansal VS

    更新日期:2008-07-15 00:00:00

  • Synthesis, structural characterization and antitumor activity evaluations of copper complex with tetraazamacrocyclic ligand.

    abstract::Cu (II) complex with 1,4,7,10-tetrakis(2-cyanoethyl-)-1,4,7,10-tetraazacyclododecane was prepared and characterized by X-ray diffraction. Four nitrogen atoms of macrocyclic ligand and oxygen atom of water molecule defined a tetragonal pyramidal polyhedron surrounding the central copper atom. Preliminary pharmacologica...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Kong D,Qin C,Meng L,Xie Y

    更新日期:1999-04-19 00:00:00

  • Discovery of pyrazolopyrimidines as the first class of allosteric agonists for the high affinity nicotinic acid receptor GPR109A.

    abstract::Pyrazolopyrimidines were discovered as the first class of allosteric agonists for the high affinity nicotinic acid receptor GPR109A. In addition to its intrinsic activity, compound 9n significantly enhances nicotinic acid binding to the receptor, thereby potentiating the functional efficacy of nicotinic acid. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Shen HC,Taggart AK,Wilsie LC,Waters MG,Hammond ML,Tata JR,Colletti SL

    更新日期:2008-09-15 00:00:00

  • Uncarinic acids: phospholipase Cgamma1 inhibitors from hooks of Uncaria rhynchophylla.

    abstract::Bioactivity-guided fractionation of the CHCl3 extract from hooks of Uncaria rhynchophylla led to the isolation of two triterpene esters, namely uncarinic acids A (1) and B (2). Their structures were established by spectroscopic and chemical methods. These compounds inhibited phospholipase Cgamma1 with IC50 values of 3...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Lee JS,Yang MY,Yeo H,Kim J,Lee HS,Ahn JS

    更新日期:1999-05-17 00:00:00

  • Solid-phase synthesis and bioevaluation of lupeol-based libraries as antimalarial agents.

    abstract::The use of the triterpenoid lupeol as a scaffold for the synthesis of lupeol-based libraries is described. Lupeol was anchored to a solid support (Rink amide/Sieber Amide) through aliphatic dicarboxylic acid moieties, which also served as a site for introducing diversity. The resulting polymer linked 3beta-O (resin-al...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Srinivasan T,Srivastava GK,Pathak A,Batra S,Raj K,Singh K,Puri SK,Kundu B

    更新日期:2002-10-21 00:00:00

  • 5-Aminomethylquinoxaline-2,3-diones. Part I: A novel class of AMPA receptor antagonists.

    abstract::A series of 5-aminomethylquinoxaline-2,3-diones have been identified as potent and selective AMPA antagonists. Some of these compounds are also active at the glycine-binding site of the NMDA receptors. A number of these novel, water-soluble quinoxaline-2,3-dione derivatives display protective effects in the electrosho...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Auberson YP,Bischoff S,Moretti R,Schmutz M,Veenstra SJ

    更新日期:1998-01-06 00:00:00

  • Synthesis and structure-activity relationships of a novel and selective bone morphogenetic protein receptor (BMP) inhibitor derived from the pyrazolo[1.5-a]pyrimidine scaffold of dorsomorphin: the discovery of ML347 as an ALK2 versus ALK3 selective MLPCN

    abstract::A structure-activity relationship of the 3- and 6-positions of the pyrazolo[1,5-a]pyrimidine scaffold of the known BMP inhibitors dorsomorphin, 1, LDN-193189, 2, and DMH1, 3, led to the identification of a potent and selective compound for ALK2 versus ALK3. The potency contributions of several 3-position substituents ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Engers DW,Frist AY,Lindsley CW,Hong CC,Hopkins CR

    更新日期:2013-06-01 00:00:00

  • Discovery and optimization of novel constrained pyrrolopyridone BET family inhibitors.

    abstract::Novel conformationally constrained BET bromodomain inhibitors have been developed. These inhibitors were optimized in two similar, yet distinct chemical series, the 6-methyl-1H-pyrrolo[2,3-c]pyridin-7(6H)-ones (A) and the 1-methyl-1H-pyrrolo[2,3-c]pyridin-7(6H)-ones (B). Each series demonstrated excellent activity in ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Fidanze SD,Liu D,Mantei RA,Hasvold LA,Pratt JK,Sheppard GS,Wang L,Holms JH,Dai Y,Aguirre A,Bogdan A,Dietrich JD,Marjanovic J,Park CH,Hutchins CW,Lin X,Bui MH,Huang X,Wilcox D,Li L,Wang R,Kovar P,Magoc TJ,Raj

    更新日期:2018-06-01 00:00:00

  • Sulfonamido-derivatives of unsubstituted carbazoles as BACE1 inhibitors.

    abstract::A novel series of variously substituted N-[3-(9H-carbazol-9-yl)-2-hydroxypropyl]-arylsulfonamides has been synthesized and assayed for β-Secretase (BACE1) inhibitory activity. BACE1 is a widely recognized drug target for the prevention and treatment of Alzheimer's Disease (AD). The introduction of benzyl substituents ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Bertini S,Ghilardi E,Asso V,Minutolo F,Rapposelli S,Digiacomo M,Saccomanni G,Salmaso V,Sturlese M,Moro S,Macchia M,Manera C

    更新日期:2017-11-01 00:00:00

  • Synthesis and thrombolytic activity of fibrinogen fragment related cyclopeptides.

    abstract::In the modification of the fibrinogen fragment related sequences ARPAK, QRPAK GRPAK and KRPAK, the corresponding cyclo-ARPAK, cyclo-QRPAK, cyclo-GRPAK, and cyclo-KRPAK were prepared in the diluted solution. The bioassay in vivo indicated that the thrombolytic potencies of cyclo-ARPAK, cyclo-GRPAK, cyclo-QRPAK, and cyc...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Zhao M,Lin N,Wang C,Peng S

    更新日期:2003-03-10 00:00:00

  • Suzuki coupling based synthesis and in vitro cytotoxic evaluation of 7-heteroaryl-substituted camptothecin analogs.

    abstract::In an effort to discover potent antitumor agents, a series of novel C-7-heteroaryl-substituted camptothecin derivatives were designed and synthesized via microwave-promoted Suzuki coupling reaction. These analogs were then assessed for cytotoxicity against three human tumor cell lines, A549, HCT116, HT-29, and inhibit...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Wang L,Huang Y,Zhang J,Tong L,Chen Y,Lu W,Huang Q

    更新日期:2014-03-15 00:00:00

  • 2-(Aminomethyl)-benzamide-based glycine transporter type-2 inhibitors.

    abstract::Structure-activity studies on benzamide 1 obtained from library screening led to the discovery of a novel series of potent and selective glycine transporter type-2 inhibitors. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Ho KK,Appell KC,Baldwin JJ,Bohnstedt AC,Dong G,Guo T,Horlick R,Islam KR,Kultgen SG,Masterson CM,McDonald E,McMillan K,Morphy JR,Rankovic Z,Sundaram H,Webb M

    更新日期:2004-01-19 00:00:00

  • Synthesis and characterization of a perchlorotriphenylmethyl (trityl) triester radical: a potential sensor for superoxide and oxygen in biological systems.

    abstract::Synthesis and characterization of an inert perchlorotriphenylmethyl triester radical, PTM-TE, are reported. PTM-TE was prepared by a facile 3-step synthesis using Friedel-Crafts reaction of tetrachlorobenzene with chloroform followed by ethoxycarbonylation and subsequent oxidation. PTM-TE is paramagnetic and exhibits ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Dang V,Wang J,Feng S,Buron C,Villamena FA,Wang PG,Kuppusamy P

    更新日期:2007-07-15 00:00:00

  • QSAR study on pK(a) vis-à-vis physiological activity of sulfonamides: a dominating role of surface tension (inverse steric parameter).

    abstract::The paper describes the dominating role of surface tension (ST) on the modeling, monitoring, and estimating pK(a) for a large series of 43 substituted sulfonamides. Because of the direct correlation of ST with parachor (Pc) vis-a-vis molecular volume (MV), ST is considered as a steric parameter. Single as well as mult...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Thakur M,Thakur A,Khadikar PV,Supuran CT

    更新日期:2005-01-03 00:00:00

  • Synthesis of the reported structure of homocereulide and its vacuolation assay.

    abstract::Homocereulide, isolated from marine bacterium Bacillus cereus, is an analog of emetic toxin cereulide. There is no report on its structure determination and involvement in B. cereus-associated food poisoning. Homocereulide is a cyclic dodecadepsipeptide composed of l-O-Val-l-Val-d-O-Leu-d-Ala and l-O-allo-Ile-d-Val-d-...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Naka T,Hattori Y,Takenaka H,Ohta Y,Kirihata M,Tanimori S

    更新日期:2019-03-01 00:00:00