Medicinal attributes of pyrazolo[3,4-d]pyrimidines: a review.

Abstract:

:Pyrazolopyrimidines are the fused heterocyclic ring systems which structurally resemble purines which prompted biological investigations to assess their potential therapeutic significance. They are known to play a crucial role in numerous disease conditions. The advent of their first bioactivity as adenosine antagonistic property divulged their medicinal potential. Radioactivity test on mice cells, morphometric and serological tests on rat hepatocytes, antitumor testing against L1210 and P388 leukemias in mice threw light on their biophysical aspects of significance. Biochemical properties were explored via xanthine oxidase assay, antioxidant enzyme assays, Western blot analysis, mRNA expression of apoptopic genes, receptor binding assays, and tryptan blue exclusion cytotoxicity evaluation. The collective results of biochemical and biophysical properties foregrounded their medicinal significance in central nervous system, cardiovascular system, cancer, inflammation etc. The present manuscript to the best of our knowledge is the first compilation on synthesis and medicinal aspects including structure-activity relationships of pyrazolo[3,4-d]pyrimidines reported to date.

journal_name

Bioorg Med Chem

authors

Chauhan M,Kumar R

doi

10.1016/j.bmc.2013.07.027

subject

Has Abstract

pub_date

2013-09-15 00:00:00

pages

5657-68

issue

18

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(13)00647-0

journal_volume

21

pub_type

杂志文章,评审
  • 3-bromohomofascaplysin A, a fascaplysin analogue from a Fijian Didemnum sp. ascidian.

    abstract::A new fascaplysin analogue, 3-bromohomofascaplysin A (1), along with two known analogues, homofascaplysin A (2) and fascaplysin (3), were isolated from a Fijian Didemnum sp. ascidian. The absolute configurations of 3-bromohomofascaplysin A (1) and homofascaplysin A (2) were determined via experimental and theoreticall...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2011.05.046

    authors: Lu Z,Ding Y,Li XC,Djigbenou DR,Grimberg BT,Ferreira D,Ireland CM,Van Wagoner RM

    更新日期:2011-11-15 00:00:00

  • Novel chromogenic aminopeptidase substrates for the detection and identification of clinically important microorganisms.

    abstract::A series of amino acid derivatives 8-10, 42 and 43 have been prepared as chromogenic enzyme substrates in order to detect aminopeptidase activity in clinically important Gram-negative and Gram-positive bacteria. Enzymatic hydrolysis liberates the amino acid moiety and either a 4-aminophenol or a 4-dialkylaminoaniline ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2014.08.004

    authors: Cellier M,James AL,Orenga S,Perry JD,Rasul AK,Robinson SN,Stanforth SP

    更新日期:2014-10-01 00:00:00

  • Discovery of platelet-type 12-human lipoxygenase selective inhibitors by high-throughput screening of structurally diverse libraries.

    abstract::Human lipoxygenases (hLO) have been implicated in a variety of diseases and cancers and each hLO isozyme appears to have distinct roles in cellular biology. This fact emphasizes the need for discovering selective hLO inhibitors for both understanding the role of specific lipoxygenases in the cell and developing pharma...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2007.08.015

    authors: Deschamps JD,Gautschi JT,Whitman S,Johnson TA,Gassner NC,Crews P,Holman TR

    更新日期:2007-11-15 00:00:00

  • Thiopyrano[2,3-e]indol-2-ones: angelicin heteroanalogues with potent photoantiproliferative activity.

    abstract::A new class of compounds, the thiopyrano[2,3-e]indol-2-ones, bioisosters of the angular furocoumarin angelicin, was synthesized with the aim of obtaining new photochemotherapeutic agents. In particular 7,8-dimethyl-thiopyranoindolone 6c s showed a remarkable phototoxicity and a great dose UVA dependence reaching IC(50...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2008.10.002

    authors: Barraja P,Diana P,Montalbano A,Carbone A,Cirrincione G,Viola G,Salvador A,Vedaldi D,Dall'acqua F

    更新日期:2008-11-15 00:00:00

  • Doxifluridine-conjugated 2-5A analog shows strong RNase L activation ability and tumor suppressive effect.

    abstract::RNase L is activated by 2',5'-oligoadenylates (2-5A) at subnanomolar levels to cleave single-stranded RNA. We previously reported the hypothesis that the introduction of an 8-methyladenosine residue at the 2'-terminus of the 2-5A tetramer shifts the 2-5A binding site of RNase L. In this study, we synthesized various 5...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2016.06.033

    authors: Kitamura Y,Kito S,Nakashima R,Tanaka K,Nagaoka K,Kitade Y

    更新日期:2016-08-15 00:00:00

  • Adenosine receptors: new opportunities for future drugs.

    abstract::This review summarises current knowledge on adenosine receptors, an important G protein-coupled receptor. The four known adenosine receptor subtypes A1, A2A, A2B, and A3 are discussed with special reference to the opportunities for drug development. ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章,评审

    doi:10.1016/s0968-0896(98)00038-8

    authors: Poulsen SA,Quinn RJ

    更新日期:1998-06-01 00:00:00

  • Discovery of a new type of scaffold for the creation of novel tyrosinase inhibitors.

    abstract::Tyrosinase is known as the key enzyme for melanin biosynthesis, which is effective in preventing skin injury by ultra violet (UV). In past decades, tyrosinase has been well studied in the field of cosmetics, medicine, agriculture and environmental sciences, and a lot of tyrosinase inhibitors have been developed for th...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2016.07.060

    authors: Oyama T,Takahashi S,Yoshimori A,Yamamoto T,Sato A,Kamiya T,Abe H,Abe T,Tanuma SI

    更新日期:2016-09-15 00:00:00

  • Oligomers of glycamino acid.

    abstract::Glycamino acids, a family of sugar amino acids, are derivatives of C-glycosides that possesses a carboxyl group at the C-1 position and an amino group replacing one of the hydroxyl groups at either the C-2, 3, 4, or 6 position. We have prepared a series of glucose-type glycamino acids as monomeric building blocks: the...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(02)00020-2

    authors: Suhara Y,Yamaguchi Y,Collins B,Schnaar RL,Yanagishita M,Hildreth JE,Shimada I,Ichikawa Y

    更新日期:2002-06-01 00:00:00

  • Norbornyllactone-substituted xanthines as adenosine A(1) receptor antagonists.

    abstract::During the search for second-generation adenosine A(1) receptor antagonist alternatives to the clinical candidate 8-(3-oxa-tricyclo[3.2.1.0(2,4)]oct-6-yl)-1,3-dipropyl-3,7-dihydro-purine-2,6-dione (BG9719), we developed a series of novel xanthines substituted with norbornyl-lactones that possessed high binding affinit...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2006.01.021

    authors: Kiesman WF,Zhao J,Conlon PR,Petter RC,Jin X,Smits G,Lutterodt F,Sullivan GW,Linden J

    更新日期:2006-06-01 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

  • Design, synthesis and biological evaluation of cycloalkyl arylpyrimidines (CAPYs) as HIV-1 NNRTIs.

    abstract::A series of 18 cycloalkyl arylpyrimidines (CAPYs) were designed from lead compounds diarylpyrimidines (DAPYs), synthesized and evaluated for in vitro anti-HIV activity. Among them, the compound 1p displayed potent anti-HIV-1 activity against WT HIV-1 with an EC(50) value of 0.055 μM and a selectivity index (SI) >7290....

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2011.10.002

    authors: Gu SX,Yang SQ,He QQ,Ma XD,Chen FE,Dai HF,Clercq ED,Balzarini J,Pannecouque C

    更新日期:2011-12-01 00:00:00

  • Synthesis and proteasome inhibition of glycyrrhetinic acid derivatives.

    abstract::This study discovered that glycyrrhetinic acid inhibited the human 20S proteasome at 22.3microM. Esterification of the C-3 hydroxyl group on glycyrrhetinic acid with various carboxylic acid reagents yielded a series of analogs with marked improved potency. Among the derivatives, glycyrrhetinic acid 3-O-isophthalate (1...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2008.05.078

    authors: Huang L,Yu D,Ho P,Qian K,Lee KH,Chen CH

    更新日期:2008-07-15 00:00:00

  • Endoperoxide polyketides from a Chinese Plakortis simplex: further evidence of the impact of stereochemistry on antimalarial activity of simple 1,2-dioxanes.

    abstract::Chemical investigation of the organic extract obtained from the sponge Plakortis simplex collected in the South China Sea afforded five new polyketide endoperoxides (2 and 4-7), along with two known analogues (1 and 3). The stereostructures of these metabolites have been deduced on the basis of spectroscopic analysis ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2014.07.034

    authors: Chianese G,Persico M,Yang F,Lin HW,Guo YW,Basilico N,Parapini S,Taramelli D,Taglialatela-Scafati O,Fattorusso C

    更新日期:2014-09-01 00:00:00

  • Design and synthesis of 6-fluoro-2-naphthyl derivatives as novel CCR3 antagonists with reduced CYP2D6 inhibition.

    abstract::In our previous study on discovering novel types of CCR3 antagonists, we found a fluoronaphthalene derivative (1) that exhibited potent CCR3 inhibitory activity with an IC(50) value of 20 nM. However, compound 1 also inhibited human cytochrome P450 2D6 (CYP2D6) with an IC(50) value of 400 nM. In order to reduce its CY...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2008.08.006

    authors: Sato I,Morihira K,Inami H,Kubota H,Morokata T,Suzuki K,Iura Y,Nitta A,Imaoka T,Takahashi T,Takeuchi M,Ohta M,Tsukamoto S

    更新日期:2008-09-15 00:00:00

  • Synthesis, structure, molecular docking, and structure-activity relationship analysis of enamines: 3-aryl-4-alkylaminofuran-2(5H)-ones as potential antibacterials.

    abstract::Thirty-one 3-aryl-4-alkylaminofuran-2(5H)-ones were designed, prepared and tested for their antibacterial activity. Some of them showed significant antibacterial activity against Gram-positive organisms, especially against Staphylococcus aureus ATCC 25923, but all were inactive against Gram-negative organisms. Out of ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2011.01.051

    authors: Xiao ZP,He XB,Peng ZY,Xiong TJ,Peng J,Chen LH,Zhu HL

    更新日期:2011-03-01 00:00:00

  • Piperazines as nootropic agents: New derivatives of the potent cognition-enhancer DM235 carrying hydrophilic substituents.

    abstract::The piperazine ring of the potent nootropic drug DM235 has been decorated with H-bond donor and acceptor groups (CH2OH, CH2OMe, CH2OCOMe, COOEt); the aim was to insert new functional groups, suitable for further chemical manipulation. The influence of these modifications on nootropic activity was assessed by means of ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2017.02.019

    authors: Martino MV,Guandalini L,Di Cesare Mannelli L,Menicatti M,Bartolucci G,Dei S,Manetti D,Teodori E,Ghelardini C,Romanelli MN

    更新日期:2017-03-15 00:00:00

  • Globostelletins A-I, cytotoxic isomalabaricane derivatives from the marine sponge Rhabdastrella globostellata.

    abstract::Nine new isomalabaricane-derived natural products, globostelletins A-I (1-9), were isolated from the marine sponge Rhabdastrella globostellata, together with jaspolides F (10), rhabdastrellic acid-A (11), (-)-stellettin E (12), stellettins C (13) and D (14). The structures of these compounds were determined on the bas...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2010.05.029

    authors: Li J,Xu B,Cui J,Deng Z,de Voogd NJ,Proksch P,Lin W

    更新日期:2010-07-01 00:00:00

  • Synthesis and in vitro characterization of platinum(II) anticancer coordinates using FTIR spectroscopy and NCI COMPARE: A fast method for new compound discovery.

    abstract::Platinum-based drugs have been used for several decades to treat various cancers successfully. Cisplatin is the original compound in this class; it cross-links DNA, resulting in cell cycle arrest and cell death via apoptosis. Cisplatin is effective against several tumor types but exhibits toxic side effects; in additi...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2014.04.017

    authors: Berger G,Leclercqz H,Derenne A,Gelbcke M,Goormaghtigh E,Nève J,Mathieu V,Dufrasne F

    更新日期:2014-07-01 00:00:00

  • Cytotoxic T lymphocyte epitope analogues containing cis- or trans-4-aminocyclohexanecarboxylic acid residues.

    abstract::In order to improve the immunotherapeutical potential of H-Cys-Leu-Gly-Gly-Leu-Leu-Thr-Met-Val-OH (CLG) peptide, an Epstein-Barr virus (EBV) subdominant epitope derived from the membrane protein LMP2, we have synthesized and tested CLG analogues containing cis- and/or trans-4-aminocyclohexanecarboxylic acid (ACCA) rep...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(02)00033-0

    authors: Marastoni M,Bazzaro M,Micheletti F,Gavioli R,Tomatis R

    更新日期:2002-09-01 00:00:00

  • Development of a novel class of peroxisome proliferator-activated receptor (PPAR) gamma ligands as an anticancer agent with a unique binding mode based on a non-thiazolidinedione scaffold.

    abstract::We previously identified dibenzooxepine derivative 1 as a potent PPARγ ligand with a unique binding mode owing to its non-thiazolidinedione scaffold. However, while 1 showed remarkably potent MKN-45 gastric cancer cell aggregation activity, an indicator of cancer differentiation-inducing activity induced by PPARγ acti...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2019.115122

    authors: Yamamoto K,Tamura T,Nakamura R,Hosoe S,Matsubara M,Nagata K,Kodaira H,Uemori T,Takahashi Y,Suzuki M,Saito JI,Ueno K,Shuto S

    更新日期:2019-11-15 00:00:00

  • 2-Amino-4-methyl-5-phenylethyl substituted-7-N-benzyl-pyrrolo[2,3-d]pyrimidines as novel antitumor antimitotic agents that also reverse tumor resistance.

    abstract::Gangjee et al. recently reported a novel series of 2-amino-4-methyl-5-phenylethyl substituted-7-benzyl-pyrrolo[2,3-d]pyrimidines, some of which exhibited two digit nanomolar antitumor and antimitotic activity and were not subject to P-glycoprotein (Pgp) or multidrug resistance protein 1 (MRP1) mediated tumor resistanc...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2011.05.030

    authors: Gangjee A,Namjoshi OA,Keller SN,Smith CD

    更新日期:2011-07-15 00:00:00

  • Pharmacophore identification of a chemokine receptor (CXCR4) antagonist, T22 ([Tyr(5,12),Lys7]-polyphemusin II), which specifically blocks T cell-line-tropic HIV-1 infection.

    abstract::We have previously found that T22 ([Tyr(5,12), Lys7]-polyphemusin II) has strong anti-human immunodeficiency virus (HIV) activity, and that T22 inhibits T cell-line-tropic HIV-1 infection mediated by CXCR4/fusin. T22 is an 18-residue peptide amide, which takes an antiparallel beta-sheet structure that is maintained by...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(98)00061-3

    authors: Tamamura H,Imai M,Ishihara T,Masuda M,Funakoshi H,Oyake H,Murakami T,Arakaki R,Nakashima H,Otaka A,Ibuka T,Waki M,Matsumoto A,Yamamoto N,Fujii N

    更新日期:1998-07-01 00:00:00

  • The design and optimization of a series of 2-(pyridin-2-yl)-1H-benzimidazole compounds as allosteric glucokinase activators.

    abstract::The optimization of a series of benzimidazole glucokinase activators is described. We identified a novel and potent achiral benzimidazole derivative as an allosteric GK activator. This activator was designed and synthesized via removal of the chiral center of the lead compound, 6-(N-acylpyrrolidin-2-yl)benzimidazole. ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2009.05.037

    authors: Takahashi K,Hashimoto N,Nakama C,Kamata K,Sasaki K,Yoshimoto R,Ohyama S,Hosaka H,Maruki H,Nagata Y,Eiki J,Nishimura T

    更新日期:2009-10-01 00:00:00

  • Peptide T-araC conjugates: solid-phase synthesis and biological activity of N4-(acylpeptidyl)-araC.

    abstract::Due to the capability of peptidyl derivatives of araC to behave as prodrugs of this antimetabolite, and because of the well known biological properties of peptide T and its analogues (in particular that of targeting CD4+ cells), new peptide T-araC conjugates were prepared and tested in vitro for antiproliferative acti...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(99)00317-x

    authors: Manfredini S,Marastoni-M,Tomatis R,Durini E,Spisani S,Pani A,Marceddu T,Musiu C,Marongiu ME,La Colla P

    更新日期:2000-03-01 00:00:00

  • Cloning, isolation and characterization of the Thermotoga maritima KDPG aldolase.

    abstract::The Thermotoga maritima aldolase gene has been cloned into a T7 expression vector and overexpressed in Escherichia coli. The preparation yields 470 UL(-1) of enzyme at a specific activity of 9.4 U mg(-1). During retroaldol cleavage of KDPG, the enzyme shows a k(cat) that decreases with decreasing temperature. A more t...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(01)00307-8

    authors: Griffiths JS,Wymer NJ,Njolito E,Niranjanakumari S,Fierke CA,Toone EJ

    更新日期:2002-03-01 00:00:00

  • Antiproliferative activities of halogenated pyrrolo[3,2-d]pyrimidines.

    abstract::In vitro evaluation of the halogenated pyrrolo[3,2-d]pyrimidines identified antiproliferative activities in compounds 1 and 2 against four different cancer cell lines. Upon screening of a series of pyrrolo[3,2-d]pyrimidines, the 2,4-Cl compound 1 was found to exhibit antiproliferative activity at low micromolar concen...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2015.06.025

    authors: Temburnikar KW,Ross CR,Wilson GM,Balzarini J,Cawrse BM,Seley-Radtke KL

    更新日期:2015-08-01 00:00:00

  • Identification of a new class of potent Cdc7 inhibitors designed by putative pharmacophore model: Synthesis and biological evaluation of 2,3-dihydrothieno[3,2-d]pyrimidin-4(1H)-ones.

    abstract::Cell division cycle 7 (Cdc7) is a serine/threonine kinase that plays important roles in the regulation of DNA replication process. A genetic study indicates that Cdc7 inhibition can induce selective tumor-cell death in a p53-dependent manner, suggesting that Cdc7 is an attractive target for the treatment of cancers. I...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2017.02.021

    authors: Kurasawa O,Oguro Y,Miyazaki T,Homma M,Mori K,Iwai K,Hara H,Skene R,Hoffman I,Ohashi A,Yoshida S,Ishikawa T,Cho N

    更新日期:2017-04-01 00:00:00

  • 1,2,3-triazole-, arylamino- and thio-substituted 1,4-naphthoquinones: potent antitumor activity, electrochemical aspects, and bioisosteric replacement of C-ring-modified lapachones.

    abstract::1,2,3-Triazole-, arylamino- and thio-substituted naphthoquinones (24, 8, and 2 representatives, respectively) were synthesized in moderate yields and evaluated against several human cancer cell lines (blood, ovarian, breast, central nervous system, colon, and prostate cancers and melanoma), showing, for some of them, ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2014.01.033

    authors: da Cruz EH,Hussene CM,Dias GG,Diogo EB,de Melo IM,Rodrigues BL,da Silva MG,Valença WO,Camara CA,de Oliveira RN,de Paiva YG,Goulart MO,Cavalcanti BC,Pessoa C,da Silva Júnior EN

    更新日期:2014-03-01 00:00:00

  • Design, synthesis, and evaluation of Leu*Ala hydroxyethylene-based non-peptide beta-secretase (BACE) inhibitors.

    abstract::With the aim of developing small molecular non-peptide beta-secretase (BACE) inhibitors, Leu*Ala hydroxyethylene (HE) was investigated as a scaffold to design and synthesize a series of compounds. Taking advantage of efficient combinatorial synthesis approaches and molecular modeling, extensive structure-activity rela...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2006.02.024

    authors: Xiao K,Li X,Li J,Ma L,Hu B,Yu H,Fu Y,Wang R,Ma Z,Qiu B,Li J,Hu D,Wang X,Shen J

    更新日期:2006-07-01 00:00:00

  • New carbocyclic nucleoside analogues with a bicyclo[2.2.1]heptane fragment as sugar moiety; synthesis, X-ray crystallography and anticancer activity.

    abstract::An amine group was synthesized starting from an optically active bicyclo[2.2.1]heptane compound, which was then used to build the 5 atoms ring of a key 6-chloropurine intermediate. This was then reacted with ammonia and selected amines obtaining new adenine- and 6-substituted adenine conformationally constrained carbo...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2013.10.056

    authors: Tănase CI,Drăghici C,Căproiu MT,Shova S,Mathe C,Cocu FG,Enache C,Maganu M

    更新日期:2014-01-01 00:00:00