17659-78-8

Basic information

• Product Name: N-isopentyladenosine
• Synonyms: N-isopentyladenosine;N-(3-Methylbutyl)adenosine;Adenosine, N-(3-methylbutyl)-;Einecs 241-638-1
• CAS NO: 17659-78-8
• Molecular Formula: C₁₅H₂₃N₅O₄
• Molecular Weight: 337.37422
• EINECS: 241-638-1
• Mol File: 17659-78-8.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 632.9 °C at 760 mmHg
• Flash Point: 336.5 °C
• Appearance: /
• Density: 1.57
• Vapor Pressure: 6.93E-17mmHg at 25°C
• Refractive Index: 1.708
• PKA: 13.12±0.70(Predicted)
• CAS DataBase Reference: N-isopentyladenosine(CAS DataBase Reference)
• NIST Chemistry Reference: N-isopentyladenosine(17659-78-8)
• EPA Substance Registry System: N-isopentyladenosine(17659-78-8)

Safety Data

• Hazardous Substances Data: 17659-78-8(Hazardous Substances Data)

Usage

General Description

N-isopentyladenosine is a chemical compound that belongs to the class of adenine derivatives and is a modified form of adenosine. It is synthesized in the body and has been implicated in various biological processes, including the regulation of gene expression and cell signaling. N-isopentyladenosine has been studied for its potential therapeutic applications, particularly in the field of cancer research, due to its ability to inhibit cell proliferation and induce apoptosis in cancer cells. Additionally, it has shown promise in the treatment of central nervous system disorders, due to its neuroprotective and anti-inflammatory properties. Research on N-isopentyladenosine continues to uncover its potential uses and mechanisms of action, making it an intriguing compound for further study and development.

InChI:InChI=1/C15H23N5O4/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/h6-9,11-12,15,21-23H,3-5H2,1-2H3,(H,16,17,18)/t9-,11-,12-,15-/m1/s1

Upstream product

• 107-85-7 1-amino-3-methylbutane 
• 2004-06-0 6-Chloropurine riboside 
• 58-63-9 Inosine 
• 3181-38-2 2',3',5'-tri-O-acetylinosine 
• 5987-73-5 2',3',5'-O-triacetyl-6-chloroinosine 

Relevant articles and documents

N6-isopentenyladenosine a new potential anti-angiogenic compound that targets human microvascular endothelial cells in vitro

N6-isopentenyladenosine is an anti-proliferative and pro-apoptotic atypical nucleoside for normal and tumor cells. Considering the role of angiogenesis in various diseases, we investigated the cytotoxic effect of N6-isopentenyladenosine on human microvascular endothelial cells, protagonists in angiogenesis. Our results show that N6-isopentenyladenosine induced a significant reduction of cell viability, upregulated p21 and promoted caspase-3 cleavage in a dose dependent manner leading to apoptotic cell death as detected by FACS analysis. To understand structure-function relationship of N6-isopentenyladenosine, we investigated the effect of some N6-isopentenyladenosine analogs. Our results suggest that N6-isopentenyladenosine and some of its derivatives are potentially novel angiostatic agents and might be associated with other anti-angiogenic compounds for a better outcome.

N6-Alkyladenosines: Synthesis and evaluation of in vitro anticancer activity

A series of adenosine analogues differently substituted in N 6-position were synthesized to continue our studies on the relationships between structure and biological activity of iPA. The structures of the compounds were confirmed by standard studies of 1H NMR, MS and elemental analysis. These molecules were then evaluated for their anti-proliferative activity on bladder cancer cells. We found that some of these compounds possess anti-proliferative activity but have no effect on cell invasion and metalloprotease activity.

Selective tight binding inhibitors of trypanosomal glyceraldehyde-3- phosphate dehydrogenase via structure-based drug design

Glyceraldehyde-3-phosphate dehydrogenase (GAPDH) from the sleeping sickness parasite Trypanosoma brucei is a rational target for anti- trypanosomatid drug design because glycolysis provides virtually all of the energy for the bloodstream form of this parasite. Glycolysis is also an important source of energy for other pathogenic parasites including Trypanosoma cruzi and Leishmania mexicana. The current study is a continuation of our efforts to use the X-ray structures of T. brucei and L. mexicana GAPDHs containing bound NAD+ to design adenosine analogues that bind tightly to the enzyme pocket that accommodates the adenosyl moiety of NAD+. The goal was to improve the affinity, selectivity, and solubility of previously reported 2'-deoxy-2'-(3-methoxybenzamido)adenosine (1). It was found that introduction of hydroxyl functions on the benzamido ring increases solubility without significantly affecting enzyme inhibition. Modifications at the previously unexploited N6-position of the purine not only lead to a substantial increase in inhibitor potency but are also compatible with the 2'-benzamido moiety of the sugar. For N6-substituted adenosines, two successive rounds of modeling and screening provided a 330-fold gain in affinity versus that of adenosine. The combination of N6- and 2'- substitutions produced significantly improved inhibitors. N6-Benzyl (9a) and N6-2-methylbenzyl (9b) derivatives of 1 display IC50 values against L. mexicana GAPDH of 16 and 4 μM, respectively (3100- and 12500-fold more potent than adenosine). The adenosine analogues did not inhibit human GAPDH. These studies underscore the usefulness of structure-based drug design for generating potent and species-selective enzyme inhibitors of medicinal importance starting from a weakly binding lead compound.