29477-83-6

Basic information

• Product Name: narciclasine
• Synonyms: narciclasine;(13β)-1,19-Didehydro-2α,3β,4β,7-tetrahydroxy-11,12-dinor-5,19-secocrinan-6-one;(2S)-3,4,4aβ,5-Tetrahydro-2α,3β,4β,7-tetrahydroxy[1,3]dioxolo[4,5-j]phenanthridin-6(2H)-one;Lycorcidinol;(2S,3R,4S,4aR)-3,4,4a,5-Tetrahydro-2,3,4,7-tetrahydroxy-(1,3)dioxolo(4,5-j)phenanthridin-6(2H)-one;(2S-(2-alpha,3-beta,4-beta,4a-beta))-3,4,4a,5-tetrahydro-2,3,4,7-tetrahydroxy-(1,3)Dioxolo(4,5-j)phenanthridin-6(2H)-one;3,4,4a,5-Tetrahydro-2,3,4,7-tetrahydroxy-(1,3)dioxolo(4,5-j)phenanthridin-6(2H)-one;BRN 1087400
• CAS NO: 29477-83-6
• Molecular Formula: C₁₄H₁₃NO₇
• Molecular Weight: 307.257
• Mol File: 29477-83-6.mol
• Article Data: 9

Chemical Properties

• Melting Point: 250-252℃
• Boiling Point: 447.77°C (rough estimate)
• Flash Point: 397.6oC
• Appearance: white to off-white/
• Density: 1.85±0.1 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 1.31E-22mmHg at 25°C
• Refractive Index: 1.5300 (estimate)
• Storage Temp.: Store at -20°C
• Solubility: DMSO: ≥10mg/mL
• PKA: 7.72±0.70(Predicted)
• CAS DataBase Reference: narciclasine(CAS DataBase Reference)
• NIST Chemistry Reference: narciclasine(29477-83-6)
• EPA Substance Registry System: narciclasine(29477-83-6)

Safety Data

• Hazard Codes: Xn
• Statements: 46
• Safety Statements: 36
• Hazardous Substances Data: 29477-83-6(Hazardous Substances Data)

Usage

Description

Different sources of media describe the Description of 29477-83-6 differently. You can refer to the following data:
1. The bulbs of several Narcissus species contain this alkaloid which crystallizes in the form of pale yellow needles with a pronounced yellow-green fluorescence. It is best purified by recrystallization from either acetic acid or an aqueous mixture of methoxyethyl alcohol. It is dextrorotatory with [α]589 + 145° or [Qh64 + 983° (c 1.5, EtOH). The ultraviolet spectrum in neutral solution (EtOH) has absorption maxima at 252, 302 and 329 mil, while that in alkaline solution (0.01 N/NaOH) has the maxima at 219, 249,310 and 355 mil. The O-methyl ether forms shiny needles which also exhibit a strong blue fluorescence. The tri_x0002_acetate has been prepared as an amorphous, non-crystallizable substance. With FeC13 the alkaloid gives a violet colour.
2. Narciclasine is a plant growth inhibitor that can be isolated from Narcissus bulbs. At 1 μM, it has been shown to induce apoptosis-mediated cytotoxicity in human cancer cells in vitro but not in normal fibroblasts. Narciclasine has been shown to regulate the Rho/Rho kinase/LIM kinase/cofilin signaling pathway by increasing GTPase RhoA activity, as well as inducing actin stress fiber formation in a RhoA-dependent manner.

Uses

Different sources of media describe the Uses of 29477-83-6 differently. You can refer to the following data:
1. Narciclasine is an antiproliferative and pro-apoptotic inducer.
2. Narciclasine is reasonably abundant in some Narcissus spp. and has served as a very useful intermediate for synthetic conversion into (+)-pancratistatin and to conduct a series of structure–activity relationship studies . Bicolorine, another member of the narciclasine series, is an unusual, completely aromatized quaternary alkaloid with an N-methyl group.

Definition

ChEBI: A natural product found in Narcissus pseudonarcissus.

References

Ceriotti., Nature, 213,595 (1967)Piozzi et al., Tetrahedron, 24, 1119 (1968)Revised structure: Mondon, Krohn., Tetrahedron Lett., 2123 (1970)Savona, Piozzi, Marino., Chern. Cornrnun., 1006 (1970)Absolute configuration: Fuganti, Mazza.,J. Chern. Soc., Chern. Cornrnun., 239 (1972)Crystal structure: Immirzi, Fuganti., J. Chern. Soc., Chern. Cornrnun., 240 (1972)Stereochemistry: Mondon, Krohn., Tetrahedron Lett., 2085 (1972)

InChI:InChI=1/C14H13NO7/c16-6-1-5-4-2-7-13(22-3-21-7)11(18)8(4)14(20)15-9(5)12(19)10(6)17/h1-2,6,9-10,12,16-19H,3H2,(H,15,20)/t6-,9+,10+,12-/m0/s1

Upstream product

• 40041-97-2 (2S,5aS,2aR,5bR)-2,8-dihydroxy-4,4-dimethyl-2,6,2a,5a,5b-pentahydro-10H-1,3-dioxolano<4,5-c>1,3-dioxoleno<4,5-j>phenanthridin-7-one 
• 7797-83-3 2H-benzo[d]1,3-dioxolane-4-carbaldehyde 
• 474526-61-9 (1R,2R,3S,4R,4aR,10bS)-1-acetoxy-2-((t-butyldimethylsilyl)oxy)-7-(o-carbamoyloxypiperonyl)-3,4-(isopropylidenedioxy)-8,9-(methylenedioxy)-1,1a,2,3,4,4a,5,6-octahydrophenanthridine 
• 474526-55-1 (1S,2S,3S,6R)-3-((t-butyldimethylsilyl)oxy)-1,2-O-isopropylidene-6-(N-(p-nitrobenzenesulfonyl)amino)cyclohexene-1,2-diol 
• 1027964-46-0 diethyl-carbamic acid 5-formyl-benzo[1,3]dioxol-4-yl ester 
• 137775-67-8 (1S,4R,5S,6R)-(-)-4-Amino-5,6-O-isopropylidenedioxycyclohex-2-en-1-ol 
• 23780-59-8 4-hydroxybenzo[d][1,3]dioxole-5-carbaldehyde 
• 80409-75-2 cis-2,2-dimethyl-3a,7a-dihydrobenzo[1,3]dioxole 
• 474526-63-1 (2S,3S,4R,4aR)-5-(t-butoxycarbonyl)-2-((t-butyldimethylsilyl)oxy)-7-(o-carbamoyloxypiperonyl)-3,4-(isopropylidenedioxy)-8,9-(methylenedioxy)-2,3,4,4a-tetrahydrophenanthridone 
• 28245-31-0 (2S,3R,4S,4aR)-2,3,4-trihydroxy-7-methoxy-3,4,4a,5-tetrahydro-[1,3]dioxolo[4,5-j]phenanthridin-6(2H)-one 
• 55623-92-2 (3aS)-12c-hydroxy-6-methoxy-2,2-dimethyl-(3ar,3bt,12ac)-3b,4,12,12a-tetrahydro-3aH-bis[1,3]dioxolo[4,5-c;4',5'-j]phenanthridin-5-one 
• 228242-68-0 methyl ((3aS,4R,7R,7aR)-7-hydroxy-7'-methoxy-2,2-dimethyl-3a,4,7,7a-tetrahydro-[5,5'-bibenzo[d][1,3]dioxol]-4-yl)carbamate 
• 228242-67-9 7-aminocarbomethoxy-2,2-dimethyl-6-(7-methoxybenzo[d][1,3]dioxol-5-yl)-(3aS,7R,7aS)-4,7-dihydro[d][1,3]dioxol-4-one 
• 228242-62-4 1,8-dibromo-11-carbomethoxy-4,4-dimethyl-(1R,2S,6S,7S)-3,5,10,11-trioxaazatricyclo[5.2.2.0^2,6]-8-undecene 

Downstream Products

• 40041-97-2 (2S,5aS,2aR,5bR)-2,8-dihydroxy-4,4-dimethyl-2,6,2a,5a,5b-pentahydro-10H-1,3-dioxolano<4,5-c>1,3-dioxoleno<4,5-j>phenanthridin-7-one 
• 40041-93-8 iso-narciclasine 
• 40042-04-4 cis-dihydronarciclasine 
• 34200-34-5 (2S,3R,4S,4aR,11bR)-2,3,4,7-tetrahydroxy-1,3,4,4a,5,11b-hexahydro-[1,3]dioxolo[4,5-j]phenanthridin-6(2H)-one 
• 29477-83-6 (2R,3R,4S,4aR)-2,3,4,7-tetrahydroxy-3,4,4a,5-tetrahydro-[1,3]dioxolo[4,5-j]phenanthridin-6(2H)-one 
• 40042-02-2 (3aS)-6-hydroxy-2,2-dimethyl-(3ar,12ac)-3a,4,11,12a-tetrahydro-bis[1,3]dioxolo[4,5-c;4',5'-j]phenanthridine-5,12-dione 
• 1019642-58-0 (2S,3S,4S,4aR)-3,4,7-trihydroxy-6-oxo-2,3,4,4a,5,6-hexahydro-[1,3]dioxolo[4,5-j]phenanthridin-2-yl acetate 
• 1417784-10-1 C₃₉H₄₇NO₈ 
• 1417784-11-2 C₃₆H₄₃NO₈ 
• 1417784-13-4 C₃₆H₄₃NO₈ 

Relevant articles and documents

ISOCARBOSTYRIL ALKALOIDS AND FUNCTIONALIZATION THEREOF

Enantioselective total syntheses of the anticancer isocarbostyril alkaloids (+)-7-deoxypancratistatin, (+)-pancratistatin, (+)-lycoricidine, and (+)-narciclasine are described. Our strategy for accessing this unique class of natural products is based on the development of a Ni-catalyzed dearomative trans-1,2-carboamination of benzene. The effectiveness of this dearomatization approach is notable, as only two additional olefin functionalizations are needed to construct the fully decorated aminocyclitol cores of these alkaloids. Installation of the lactam ring has been achieved through several pathways and a direct interconversion between natural products was established via a late-stage C-7 cupration. Using this synthetic blueprint, we were able to produce natural products on a gram scale and provide tailored analogs with improved activity, solubility, and metabolic stability.

Isolation, Synthesis, and Semisynthesis of Amaryllidaceae Constituents from Narcissus and Galanthus sp.: De Novo Total Synthesis of 2-epi-Narciclasine

An efficient protocol for the isolation of narciclasine from common Amaryllidaceae bulbs, separation from haemanthamine, and the occurrence of a trace alkaloid, 2-epi-narciclasine, are reported. Attempts to convert natural narciclasine to its C-2 epimer by Mitsunobu inversion or oxidation/reduction sequences were compromised by rearrangement and aromatization processes, through which a synthesis of the alkaloid narciprimine was achieved. The methylation of the 7-hydroxy group of natural narciclasine followed by protection of the 3,4-diol function and oxidation/reduction sequence provided the target C-2 epimer. A de novo chemoenzymatic synthesis of 2-epi-narciclasine from m-dibromobenzene is also described. Haemanthamine and narciprimine were readily detected in the crude extracts of Narcissus and Galanthus bulbs containing narciclasine, and the occurrence of 2-epi-narciclasine as a trace natural product in Galanthus sp. is reported for the first time.

Total synthesis and biological evaluation of Amaryllidaceae alkaloids: narciclasine, ent-7-deoxypancratistatin, regioisomer of 7-deoxypancratistatin, 10b-epi-deoxypancratistatin, and truncated derivatives.

Biocatalytic approaches have yielded efficient total syntheses of the major Amaryllidaceae alkaloids, all based on the key enzymatic dioxygenation of suitable aromatic precursors. This paper discusses the logic of general synthetic design for lycoricidine, narciclasine, pancratistatin, and 7-deoxypancratistatin. Experimental details are provided for the recently accomplished syntheses of narciclasine, ent-7-deoxypancratistatin, and 10b-epi-deoxypancratistatin via a new and selective opening of a cyclic sulfate over aziridines followed by aza-Payne rearrangement. The structural core of 7-deoxypancratistatin has also been degraded to a series of intermediates in which the amino inositol unit is cleaved and deoxygenated in a homologous fashion. These truncated derivatives and the compounds from the synthesis of the unnatural derivatives have been tested against six important human cancer cell lines in an effort to further develop the understanding of the mode of action for the most active congener in this group, pancratistatin. The results of the biological activity testing as well as experimental, spectral, and analytical data are provided in this manuscript for all relevant compounds.