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

S-Adenosylhomocysteine (SAH) hydrolase catalyzes the reversible hydrolysis of SAH to adenosine and homocysteine. The inhibition of SAH hydrolase causes the intracellular accumulation of SAH, elevating the ratio of SAH to S-adenosylmethionine (SAM) and inhibiting SAM-dependent methyltransferase. (?)-Neplanocin A potently and irreversibly inactivates SAH hydrolase (Ki = 8.39 nM). It has antitumor activity against mouse leukemia L1210 cells and broad-spectrum antiviral activity. Neplanocin A is more potent against vesicular stomatitis than the reversible SAH hydrolase inhibitor 3-deazaneplanocin (ID50 = 0.07 and 0.3 μg/ml, respectively).

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

• 952418-11-0 (1R,4R,5S)-9-[3-(tert-butyldiphenylsilyloxymethyl)-4,5-isopropylidenedioxy-2-cyclopenten-1-yl]-N⁶,N⁶-bis(tert-butoxycarbonyl)adenine 
• 952418-12-1 (1R,4R,5S)-9-[3-(tert-butyldiphenylsilyloxymethyl)-4,5-isopropylidenedioxy-2-cyclopenten-1-yl]adenine 
• 10257-32-6 D-ribose 
• 4157-02-2 cis 2-cyclopentene 1,4-dibenzoate 
• 114933-42-5 Acetic acid (3aS,4S,6aS)-4-benzyloxymethyl-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yl ester 
• 114933-43-6 Acetic acid (3aS,4S,6aR)-6-benzyloxymethyl-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yl ester 
• 210897-59-9 C₁₇H₂₉BrO₄Si 
• 210897-48-6 Acetic acid (1S,3aR,4R,7S,7aR)-1-hydroxy-1,4,7,7a-tetrahydro-4,7-methano-inden-3a-ylmethyl ester 
• 210897-52-2 C₁₁H₁₃BrO₂ 
• 160343-78-2 (3aR,6aR)-6-{{[(1,1-dimethylethyl)dimethylsilyl]oxy}methyl}-3a,6a-dihydro-2,2-dimethyl-4H-cyclopenta[d]-1,3-dioxol-4-one 
• 160343-79-3 (3aS,4S,6aR)-6-{{[(1,1-dimethylethyl)dimethylsilyl]oxy}methyl}-3a,6a-dihydro-2,2-dimethyl-4H-cyclopenta[d]-1,3-dioxol-4-ol 
• 121312-57-0 ethyl 5-oxo-tricyclo[5.2.1.0.]deca-3,8-diene-2-carboxylate 
• 288866-44-4 (1'S,2'R,3'S,4'R)-1'-acetyloxymethyl-4'-(6-chloropurin-9-yl)-2',3'-diacetyloxy-1'-hydroxycyclopent-1'-ene 
• 188907-71-3 (1'S,2'S,3'S,4'R)-4'-(6-chloropurin-9-yl)-1'-hydroxymethyl-1'',1',2',3'-bis-O-isopropylidene-cyclopentane-1',2',3'-triol 

Downstream Products

• 83844-30-8 N⁶-benzoyl-9-<(1R,2S,3R)-2,3-dihydroxy-4-(hydroxymethyl)-4-cyclopenten-1-yl>adenine 
• 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 

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