114987-19-8

Basic information

• Product Name: cytallene
• Synonyms: cytallene;1-(4-Hydroxy-1,2-butadienyl)cytosine
• CAS NO: 114987-19-8
• Molecular Formula: C₈H₉N₃O₂
• Molecular Weight: 179.18
• Mol File: 114987-19-8.mol
• Article Data: 2

Chemical Properties

• Melting Point: 193-195 °C(Solv: methanol (67-56-1))
• Boiling Point: 393.1°Cat760mmHg
• Flash Point: 191.6°C
• Appearance: /
• Density: 1.28g/cm³
• Vapor Pressure: 8.26E-08mmHg at 25°C
• Refractive Index: 1.595
• PKA: 14.36±0.10(Predicted)
• CAS DataBase Reference: cytallene(CAS DataBase Reference)
• NIST Chemistry Reference: cytallene(114987-19-8)
• EPA Substance Registry System: cytallene(114987-19-8)

Safety Data

• Hazardous Substances Data: 114987-19-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C8H9N3O2/c9-7-3-5-11(8(13)10-7)4-1-2-6-12/h2-5,12H,6H2,(H2,9,10,13)

Upstream product

• 114987-16-5 N¹-(4-Chloro-2-butyn-1-yl)cytosine 
• 168975-54-0 (+/-)-N⁴-benzoylcytallene 
• 114987-17-6 9-<4-hydroxybut-2-yn-1-yl>cytosine 

Downstream Products

• 168975-54-0 (+/-)-N⁴-benzoylcytallene 

Relevant articles and documents

Synthesis, Absolute Configuration, and Enantioselectivity of Antiretroviral Effect of (R)-(-)- and (S)-(+)-Cytallene. Lipase-Catalyzed Enantioselective Acylations of (+/-)-N4-Acylcytallenes

Enantioselectivity of acylations of (+/-)-cytallene (1b), (+/-)-N4-acetylcytallene (11a), (+/-)-N4-benzoylcytallene (11b), and (+/-)-N4-(9-fluorenylmethoxycarbonyl)cytallene (11c) using vinyl butyrate or acetate catalyzed by lipases in organic solvents was investigated.Reactions with 1b, 11a, and adenallene (1a) did not display a high enantioselectivity but all resulted in a predominant acylation of the (-)-enantiomers.Application of the Lowe-Brewster rule led to a tentative assignment of the R-configuration to all acylated products.Studies of the time course of acylation of (+/-)-N4-benzoylcytallene (11b) in chloroform, tetrahydrofuran (THF), tetrahydropyran (THP), tetrahydrothiophene (THT), and dioxane with lipase PS30 and/or AK showed that the reaction in THF catalyzed by lipase AK was the most promising for resolution of 11b.Indeed, a large-scale acylation afforded, after separation and deprotection of intermediates 3e and 10d, (+)- and (-)-cytallene (3c and 2b) in high yield and enantioselectivity.Acylation of 11c in THF led also to formation of 3c and 2b in high enantioselectivity.Single crystal X-ray diffraction established the S-configuration of (+)-cytallene (3c), thus confirming the assignment made on the basis of Lowe-Brewster rule.An improved large-scale synthesis of (+/-)-cytallene (1b) is also described.The R-enantiomer 2b inhibited the replication of a primary human immunodeficiency virus (HIV-1) isolate in phytohemagglutinin-activated peripheral blood mononuclear cells (PHA-PBM) with IC50 0.4 and IC90 1.7 μM. (+/-)-Cytallene (1b) exhibited IC50 0.8 and IC90 3.4 μM.Both compounds completely suppressed replication of HIV-1 at 10 μM with no detecable cytotoxicity.The S-enantiomer (3c) was inactive.