200,000+ products from a single source!

sales@angenechem.com

Home > Other Building Blocks > 7724-76-7

7724-76-7

7724-76-7 | N6-(3-Methyl-2-butenyl);adenosine

CAS No: 7724-76-7 Catalog No: AG003SOA MDL No:MFCD00005741

Product Description

Catalog Number:
AG003SOA
Chemical Name:
N6-(3-Methyl-2-butenyl);adenosine
CAS Number:
7724-76-7
Molecular Formula:
C15H21N5O4
Molecular Weight:
335.3583
MDL Number:
MFCD00005741
IUPAC Name:
(2R,3S,4R,5R)-2-(hydroxymethyl)-5-[6-(3-methylbut-2-enylamino)purin-9-yl]oxolane-3,4-diol
InChI:
InChI=1S/C15H21N5O4/c1-8(2)3-4-16-13-10-14(18-6-17-13)20(7-19-10)15-12(23)11(22)9(5-21)24-15/h3,6-7,9,11-12,15,21-23H,4-5H2,1-2H3,(H,16,17,18)/t9-,11-,12-,15-/m1/s1
InChI Key:
USVMJSALORZVDV-SDBHATRESA-N
SMILES:
OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1ncnc2NCC=C(C)C
EC Number:
231-771-3
UNII:
8EU82FAZ5J

Properties

Complexity:
461  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
4  
Defined Bond Stereocenter Count:
0
Exact Mass:
335.159g/mol
Formal Charge:
0
Heavy Atom Count:
24  
Hydrogen Bond Acceptor Count:
8  
Hydrogen Bond Donor Count:
4  
Isotope Atom Count:
0
Molecular Weight:
335.364g/mol
Monoisotopic Mass:
335.159g/mol
Rotatable Bond Count:
5  
Topological Polar Surface Area:
126A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
1.1  

Literature

Title Journal
Phytohormones and willow gall induction by a gall-inducing sawfly. The New phytologist 20121001
Remodeling of cytokinin metabolism at infection sites of Colletotrichum graminicola on maize leaves. Molecular plant-microbe interactions : MPMI 20120801
Functional identification of OsHk6 as a homotypic cytokinin receptor in rice with preferential affinity for iP. Plant & cell physiology 20120701
Endogenous hormone levels and anatomical characters of haustoria in Santalum album L. seedlings before and after attachment to the host. Journal of plant physiology 20120615
Effects of the coordination mechanism between roots and leaves induced by root-breaking and exogenous cytokinin spraying on the grazing tolerance of ryegrass. Journal of plant research 20120501
Physiological and molecular analysis of the interaction between aluminium toxicity and drought stress in common bean (Phaseolus vulgaris). Journal of experimental botany 20120501
Cytokinins in shoot apices of Brassica napus plants during vernalization. Plant science : an international journal of experimental plant biology 20120501
Physiological response to drought in radiata pine: phytohormone implication at leaf level. Tree physiology 20120401
Physiological, biochemical and transcriptional analysis of onion bulbs during storage. Annals of botany 20120301
Sensitive quantification of isoprenoid cytokinins in plants by selective immunoaffinity purification and high performance liquid chromatography-quadrupole-time of flight mass spectrometry. Methods (San Diego, Calif.) 20120201
Phytohormone production and colonization of canola (Brassica napus L.) roots by Pseudomonas fluorescens 6-8 under gnotobiotic conditions. Canadian journal of microbiology 20120201
A liquid chromatography tandem mass spectrometry method for simultaneous determination of acid/alkaline phytohormones in grapes. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20120115
The pea TCP transcription factor PsBRC1 acts downstream of Strigolactones to control shoot branching. Plant physiology 20120101
Effect of blue light on endogenous isopentenyladenine and endoreduplication during photomorphogenesis and de-etiolation of tomato (Solanum lycopersicum L.) seedlings. PloS one 20120101
Effects of cytokinins, cytokinin ribosides and their analogs on the viability of normal and neoplastic human cells. Anticancer research 20111001
Antiproliferative activity of N(6)-isopentenyladenosine on HCT-15 colon carcinoma cell line. Nucleic acid therapeutics 20111001
Transformations of the natural cytokinin N6-isopentenyladenine in aqueous acidic media: structural aspects. Organic & biomolecular chemistry 20110821
Elevated carbon dioxide and/or ozone concentrations induce hormonal changes in Pinus tabulaeformis. Journal of chemical ecology 20110701
1H, 13C and 15N NMR spectral assignments of adenosine derivatives with different amino substituents at C6-position. Magnetic resonance in chemistry : MRC 20110501
Characterization of a single recessive yield trait mutant with elevated endogenous ABA concentration and deformed grains, spikelets and leaves. Plant science : an international journal of experimental plant biology 20110201
The phenylquinazoline compound S-4893 is a non-competitive cytokinin antagonist that targets Arabidopsis cytokinin receptor CRE1 and promotes root growth in Arabidopsis and rice. Plant & cell physiology 20101201
Antiproliferative activity of N6-isopentenyladenosine on MCF-7 breast cancer cells: cell cycle analysis and DNA-binding study. DNA and cell biology 20101101
[Variation of endogenous hormones in formation of microtuber of Dioscorea opposite in vitro]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20101101
Involvement of Akt/NF-κB pathway in N6-isopentenyladenosine-induced apoptosis in human breast cancer cells. Molecular carcinogenesis 20101001
1H, 13C and 15N NMR assignments for N6-isopentenyladenosine/inosine analogues. Magnetic resonance in chemistry : MRC 20100901
Anticancer activity of natural cytokinins: a structure-activity relationship study. Phytochemistry 20100801
Effect on shoot water relations, and cytokinin and abscisic acid levels of inducing expression of a gene coding for isopentenyltransferase in roots of transgenic tobacco plants. Journal of experimental botany 20100801
Synthesis and evaluation of in vitro anticancer activity of some novel isopentenyladenosine derivatives. Bioorganic & medicinal chemistry 20100615
Influence of plant maturity, shoot reproduction and sex on vegetative growth in the dioecious plant Urtica dioica. Annals of botany 20091001
Functional analyses of LONELY GUY cytokinin-activating enzymes reveal the importance of the direct activation pathway in Arabidopsis. The Plant cell 20091001
Novel isopentenyladenosine analogues: synthesis, characterization, and evaluation of antiproliferative activity on bladder carcinoma cells. Nucleosides, nucleotides & nucleic acids 20090801
Snapshots of dynamics in synthesizing N(6)-isopentenyladenosine at the tRNA anticodon. Biochemistry 20090616
Pharmacogenomics and analogues of the antitumour agent N6-isopentenyladenosine. International journal of cancer 20090501
Gene expression profiles in differentiating leukemia cells induced by methyl jasmonate are similar to those of cytokinins and methyl jasmonate analogs induce the differentiation of human leukemia cells in primary culture. Leukemia 20090401
N6-isopentenyladenosine inhibits cell proliferation and induces apoptosis in a human colon cancer cell line DLD1. International journal of cancer 20090315
Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors. Journal of medicinal chemistry 20081113
Expression of class I knotted1-like homeobox genes in the storage roots of sweetpotato (Ipomoea batatas). Journal of plant physiology 20081101
Induction of in vitro flowering in Dendrobium Madame Thong-In (Orchidaceae) seedlings is associated with increase in endogenous N(6)-(Delta (2)-isopentenyl)-adenine (iP) and N (6)-(Delta (2)-isopentenyl)-adenosine (iPA) levels. Plant cell reports 20080801
Involvement of polyamines in the post-anthesis development of inferior and superior spikelets in rice. Planta 20080601
Cytokinins induce sporulation in Dictyostelium. Development (Cambridge, England) 20080301
Biological and pharmacological roles of N6-isopentenyladenosine: an emerging anticancer drug. Anti-cancer agents in medicinal chemistry 20080201
[Change of endogenous hormone around sprout tumble of Pinellia ternata under high temperature stress]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20071201
Characterisation of a prokaryote-type tRNA-isopentenyltransferase gene from the moss Physcomitrella patens. Planta 20070801
[Effects of elevated atmospheric CO2 concentration on endogenous hormones in gingko leaves]. Ying yong sheng tai xue bao = The journal of applied ecology 20070701
N6-isopentenyladenosine: a potential therapeutic agent for a variety of epithelial cancers. International journal of cancer 20070615
Feedback regulation of xylem cytokinin content is conserved in pea and Arabidopsis. Plant physiology 20070301
Thidiazuron influences the endogenous levels of cytokinins and IAA during the flowering of isolated shoots of Dendrobium. Journal of plant physiology 20061101
N6-isopentenyladenosine arrests tumor cell proliferation by inhibiting farnesyl diphosphate synthase and protein prenylation. FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20060301
[Dynamics of soluble sugar and endogenous hormone contents in several steppe grass species during their germination period in spring]. Ying yong sheng tai xue bao = The journal of applied ecology 20060201
AMPK or ZMPK? Medical hypotheses 20060101
Artificial cell-cell communication in yeast Saccharomyces cerevisiae using signaling elements from Arabidopsis thaliana. Nature biotechnology 20051201
Immediate up-regulation of the calcium-binding protein S100P and its involvement in the cytokinin-induced differentiation of human myeloid leukemia cells. Biochimica et biophysica acta 20050910
Squash xylem sap has activities that inhibit proliferation and promote the elongation of tobacco BY-2 cell protoplasts. Plant physiology and biochemistry : PPB 20050501
Induction of CCAAT/enhancer binding protein-delta by cytokinins, but not by retinoic acid, during granulocytic differentiation of human myeloid leukaemia cells. British journal of haematology 20050201
Changes of zeatin riboside content in rice plants due to infestation by Nilaparvata lugens (Homoptera: Delphacidae). Journal of economic entomology 20041201
Analysis of CDK2 active-site hydration: a method to design new inhibitors. Proteins 20040501
Metal ion stabilization of the U-turn of the A37 N6-dimethylallyl-modified anticodon stem-loop of Escherichia coli tRNAPhe. Biochemistry 20040113
Investigation of cytokinin-deficient phenotypes in Arabidopsis by ectopic expression of orchid DSCKX1. FEBS letters 20031204
Alterations in endogenous levels of cytokinins following grafting of Pinus radiata support ratio of cytokinins as an index of ageing and vigour. Journal of plant physiology 20031101
Amperometric immunosensor based on polypyrrole/poly(m-pheylenediamine) multilayer on glassy carbon electrode for cytokinin N6-(Delta2-isopentenyl) adenosine assay. Analytical biochemistry 20031001
A new method for enzymatic preparation of isopentenyladenine-type and trans-zeatin-type cytokinins with radioisotope-labeling. Journal of plant research 20030601
Cyclin-dependent kinase inhibitor, roscovitine, in combination with exogenous cytokinin, N6-benzyladenine, causes increase of cis-cytokinins in immobilized tobacco cells. Biotechnology letters 20030301
The Arabidopsis AtIPT8/PGA22 gene encodes an isopentenyl transferase that is involved in de novo cytokinin biosynthesis. Plant physiology 20030101
Responses of ABA and CTK to soil drought in leafless and leafy apple tree. Journal of Zhejiang University. Science 20030101
Hormonal regulation of the onset of endosperm development in amphimictic Triticum aestivum L. and apomictic Taraxacum officinale Web. species. Doklady. Biochemistry and biophysics 20030101
Regulation of sulfur-responsive gene expression by exogenously applied cytokinins in Arabidopsis thaliana. Plant & cell physiology 20021201
Amyloplast formation in cultured tobacco BY-2 cells requires a high cytokinin content. Plant & cell physiology 20021201
A trans-zeatin riboside in root xylem sap negatively regulates adventitious root formation on cucumber hypocotyls. Journal of experimental botany 20021101
Dynamics and binding modes of free cdk2 and its two complexes with inhibitors studied by computer simulations. Journal of biomolecular structure & dynamics 20021001
The Tzs protein from Agrobacterium tumefaciens C58 produces zeatin riboside 5'-phosphate from 4-hydroxy-3-methyl-2-(E)-butenyl diphosphate and AMP. FEBS letters 20020911
Differentiation of human myeloid leukemia cells by plant redifferentiation-inducing hormones. Leukemia & lymphoma 20020901
Abscisic acid and cytokinins in the root exudates and leaves and their relationship to senescence and remobilization of carbon reserves in rice subjected to water stress during grain filling. Planta 20020801
Movement to bark and metabolism of xylem cytokinins in stems of Lupinus angustifolius. Phytochemistry 20020701
Activation of caspase-like proteases and induction of apoptosis by isopentenyladenosine in tobacco BY-2 cells. Planta 20020501
Multiple routes communicating nitrogen availability from roots to shoots: a signal transduction pathway mediated by cytokinin. Journal of experimental botany 20020401
In situ localisation of cytokinins in the shoot apical meristem of Sinapis alba at floral transition. Planta 20020401
Charcoal affects early development and hormonal concentrations of somatic embryos of hybrid larch. Tree physiology 20020401
Induction of early bolting in Arabidopsis thaliana by triacontanol, cerium and lanthanum is correlated with increased endogenous concentration of isopentenyl adenosine (iPAdos). Journal of experimental botany 20020301
Water stress, CO2 and photoperiod influence hormone levels in wheat. Journal of plant physiology 20020301
Activation tagging identifies a gene from Petunia hybrida responsible for the production of active cytokinins in plants. The Plant journal : for cell and molecular biology 20020301
Conformational preferences of anticodon 3'-adjacent hypermodified nucleic acid base cis-or trans-zeatin and its 2-methylthio derivative, cis-or trans- ms(2)zeatin. Journal of biomolecular structure & dynamics 20020201
Expression and evolution of functionally distinct haemoglobin genes in plants. Plant molecular biology 20011101
Hormonal changes in the grains of rice subjected to water stress during grain filling. Plant physiology 20010901
The Arabidopsis AHK4 histidine kinase is a cytokinin-binding receptor that transduces cytokinin signals across the membrane. Plant & cell physiology 20010901
Structure-activity relationships and inhibitory effects of various purine derivatives on the in vitro growth of Plasmodium falciparum. Biochemical pharmacology 20010801
Influence of N6-isopentenyladenosine (i(6)A) on thermal stability of RNA duplexes. Biophysical chemistry 20010702
Cytokinin overproducing ove mutants of Physcomitrella patens show increased riboside to base conversion. Plant physiology 20010701
Identification of plant cytokinin biosynthetic enzymes as dimethylallyl diphosphate:ATP/ADP isopentenyltransferases. Plant & cell physiology 20010701
Transport and accumulation rates of abscisic acid and aldehyde oxidase activity in Pisum sativum L. in response to suboptimal growth conditions. Journal of experimental botany 20010601
Cytokinin production by plant growth promoting rhizobacteria and selected mutants. Canadian journal of microbiology 20010501
In situ localization of endogenous cytokinins during shooty tumor development on Eucalyptus globulus Labill. Planta 20010501
Nitrogen-dependent accumulation of cytokinins in root and the translocation to leaf: implication of cytokinin species that induces gene expression of maize response regulator. Plant & cell physiology 20010101
Cytokinin oxidase or dehydrogenase? Mechanism of cytokinin degradation in cereals. European journal of biochemistry 20010101
[A new micromethod for differential quantitative assay of zeatin and zeatin riboside]. Prikladnaia biokhimiia i mikrobiologiia 20010101
A new approach to the problem of differential quantification of zeatin and zeatin riboside. Doklady. Biochemistry and biophysics 20010101
Dynamics of the cytokinin content in different regions of the ovary in Triticum aestivum L. and Taraxacum officinale Web. during the preparation of the ovicell for division. Doklady. Biochemistry and biophysics 20010101

© 2019 Angene International Limited. All rights Reserved.