72877-50-0

Basic information

• Product Name: neplanocin A
• Synonyms: neplanocin A;A-11079B16;Antibiotic A-11079B16;Neoplanocin A;3-Neplanocin A
• CAS NO: 72877-50-0
• Molecular Formula: C₁₁H₁₃N₅O₃
• Molecular Weight: 263.256
• Mol File: 72877-50-0.mol
• Article Data: 16

Chemical Properties

• Melting Point: 214-216 °C (decomp)
• Boiling Point: 632.6°C at 760 mmHg
• Flash Point: 336.4°C
• Appearance: /
• Density: 1.91g/cm³
• Vapor Pressure: 7.18E-17mmHg at 25°C
• Refractive Index: 1.881
• PKA: 13.43±0.70(Predicted)
• CAS DataBase Reference: neplanocin A(CAS DataBase Reference)
• NIST Chemistry Reference: neplanocin A(72877-50-0)
• EPA Substance Registry System: neplanocin A(72877-50-0)

Safety Data

• Hazardous Substances Data: 72877-50-0(Hazardous Substances Data)

Usage

Description

Neplanocin A is a potent and irreversible inhibitor of S-Adenosylhomocysteine (SAH) hydrolase, an enzyme that catalyzes the reversible hydrolysis of SAH to adenosine and homocysteine. It has antitumor activity against mouse leukemia L1210 cells and broad-spectrum antiviral activity.
Used in Pharmaceutical Industry:
Neplanocin A is used as an antitumor agent for its ability to inhibit SAH hydrolase, leading to the intracellular accumulation of SAH and the inhibition of SAM-dependent methyltransferase. This results in the suppression of tumor growth and progression.
Additionally, neplanocin A is used as an antiviral agent for its broad-spectrum activity against various viruses, including vesicular stomatitis. It is more potent than the reversible SAH hydrolase inhibitor 3-deazaneplanocin, making it a promising candidate for the development of antiviral therapies.

InChI:InChI=1/C11H13N5O3/c12-10-7-11(14-3-13-10)16(4-15-7)6-1-5(2-17)8(18)9(6)19/h1,3-4,6,8-9,17-19H,2H2,(H2,12,13,14)/t6-,8-,9+/m1/s1

Upstream product

• 89291-82-7 (-)-9-<(1R,4R,5S)-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopenten-1-yl>adenine 
• 10257-32-6 D-ribose 
• 30725-00-9 2,3-O-isopropylidene-D-ribonic-γ-lactone 
• 104738-67-2 (1R,5S)-8-methoxy-3,3-dimethyl-2,4-dioxabicyclo-<3.3.0>oct-7en-6-one 
• 89505-90-8 6-Chloro-9-((3aS,4R,6aR)-6-methoxymethoxymethyl-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yl)-9H-purine 
• 123883-97-6 (3aS,6aR)-6-Methoxy-4-methoxymethoxymethyl-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-ol 
• 123883-99-8 (1S,4R,5S)-4,5-isopropylidenedioxy-3-<<(methoxy)methoxy>methyl>cyclopent-2-enol 
• 123883-98-7 (3aR,6aR)-6-Methoxymethoxymethyl-2,2-dimethyl-3a,6a-dihydro-cyclopenta[1,3]dioxol-4-one 
• 128165-49-1 (1S,4R,5R)-3-(tert-butoxymethyl)-4,5-(cyclohexylidenedioxy)-2-cyclopenten-1-ol methanesulfonate 
• 128165-45-7 (4R,5R)-3-(tert-butoxymethyl)-4,5-(cyclohexylidenedioxy)-2-cyclopenten-1-one 
• 128165-46-8 (1S,4R,5S)-3-(tert-butoxymethyl)-4,5-(cyclohexylidenedioxy)-2-cyclopenten-1-ol 
• 111005-65-3 (-)-2,3-(cyclohexylidenedioxy)-4-cyclopentenone 
• 66224-66-6 adenine 
• 89291-72-5 C₃₂H₃₅O₁₀P 

Downstream Products

• 138571-54-7 6'-(R)-methylneplanocin A 
• 138662-99-4 6'-(S)-methylneplanocin A 
• 138571-53-6 N⁶-benzoyl-9<(1R,2S,3R)-4-(1-hydroxyethyl)-2,3-(isopropylidenodioxy)-4-cyclopenten-1-yl>adenine 
• 138571-49-0 N⁶-benzoyl-9-<(1R,2S,3R)-2,3-(isopropylidenedioxy)-4-(hydroxymethyl)-4-cyclopenten-1-yl>adenine 
• 138571-50-3 N⁶-benzoyl-9<(1R,2S,3R)-4-formyl-2,3-(isopropylidenedioxy)-4-cyclopenten-1-yl>adenine 
• 138571-51-4 N⁶-benzoyl-9<(1R,2S,3R)-4-ethenyl-2,3-(isopropylidenedioxy)-4-cyclopenten-1-yl>adenine 
• 142888-07-1 C₂₇H₂₅N₅O₅ 
• 78216-79-2 ara-neplanocin A 
• 88183-83-9 N⁶,6'-dibenzoylneplanocin A 2',3'-O-cyclic thiocarbonate 
• 88183-85-1 N⁶,6'-dibenzoylneplanocin A 2',3'-cyclic carbonate 
• 84207-68-1 N⁶,6'-dibenzoylneplanocin A 
• 88183-84-0 N⁶,6'-dibenzoyl-3'-deoxyneplanocin A 
• 142888-03-7 C₂₇H₂₅N₅O₅ 
• 83844-30-8 N⁶-benzoyl-9-<(1R,2S,3R)-2,3-dihydroxy-4-(hydroxymethyl)-4-cyclopenten-1-yl>adenine 

Relevant articles and documents

Structure-Activity Relationships of Neplanocin A Analogues as S -Adenosylhomocysteine Hydrolase Inhibitors and Their Antiviral and Antitumor Activities

On the basis of the potent inhibitory activity of neplanocin A (1) against S-adenosylhomocysteine (AdoHcy) hydrolase, we analyzed the comprehensive structure-activity relationships by modifying the adenine and carbasugar moiety of 1 to find the pharmacoph

An improved approach to chiral cyclopentenone building blocks. Total synthesis of pentenomycin I and neplanocin A

An improved approach to enantiomerically pure hydroxylated cyclopentenones is reported here, which involves intramolecular nitrone cycloaddition of sugar-derived chiral pent-4-enals and hex-5-en-ones-2 followed by N-O bond cleavage, quaternization of the amine thus produced, and finally oxidative elimination of the amino group. Synthesis of pentenomycin I and neplanocin A is described following this methodology.

Palladium-catalyzed enantioselective synthesis of carbanucleosides

A general strategy has been developed for enantioselective synthesis of diverse carbanucleosides. The key step is a Pd(0)-catalyzed enantioselective allylic amination of cis-3,5-dibenzoyloxycyclopent-2-ene 10a with the nucleobase. With guanine-derived nuc