Narciclasine

Base Information

• Chemical Name: Narciclasine
• CAS No.: 29477-83-6
• Molecular Formula: C14H13 N O7
• Molecular Weight: 307.26
• European Community (EC) Number: 687-829-7
• NSC Number: 266535
• DSSTox Substance ID: DTXSID70183677
• Nikkaji Number: J53.933C
• Wikipedia: Narciclasine
• Wikidata: Q18379239
• Pharos Ligand ID: KKPULN5F9XU4
• Metabolomics Workbench ID: 143575
• ChEMBL ID: CHEMBL98745
• Mol file: 29477-83-6.mol

Synonyms:narciclasine

Chemical Property of Narciclasine

Chemical Property:

• Vapor Pressure: 1.31E-22mmHg at 25°C
• Melting Point: 250-252℃
• Refractive Index: 1.5300 (estimate)
• Boiling Point: 733.8oC at 760 mmHg
• PKA: 7.72±0.70(Predicted)
• Flash Point: 397.6oC
• PSA: 128.48000
• Density: 1.85g/cm3
• LogP: -0.95860
• Storage Temp.: Store at -20°C
• Solubility.: DMSO: ≥10mg/mL
• XLogP3: -1.2
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 0
• Exact Mass: 307.06920175
• Heavy Atom Count: 22
• Complexity: 523

Purity/Quality:

95%-98% ^*data from raw suppliers

Narciclasine ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 46
• Safety Statements: 36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1OC2=C(O1)C(=C3C(=C2)C4=CC(C(C(C4NC3=O)O)O)O)O
• Isomeric SMILES: C1OC2=C(O1)C(=C3C(=C2)C4=C[C@@H]([C@H]([C@H]([C@@H]4NC3=O)O)O)O)O
• Description: 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. 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: Narciclasine is an antiproliferative and pro-apoptotic inducer. 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.

Technology Process of Narciclasine

There total 94 articles about Narciclasine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 89.0%

C21H25N3O8 → narciclasine (29477-83-6,220751-83-7)

Guidance literature:

C₂₁H₂₅N₃O₈; With samarium diiodide; In tetrahydrofuran; methanol; at 0 - 40 ℃;

With hydrogenchloride; In tetrahydrofuran; methanol; water; at 0 ℃;

DOI:10.1021/jacs.8b12123

Reference yield: 89.0%

(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 (40041-97-2) → narciclasine (29477-83-6,220751-83-7)

Guidance literature:

With trifluoroacetic acid; at 0 ℃; for 0.166667h;

DOI:10.1021/ja9826688

Reference yield: 65.0%

(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 (474526-63-1) → narciclasine (29477-83-6,220751-83-7)

Guidance literature:

(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; With formic acid; In tetrahydrofuran; at 60 ℃; for 45h;

With lithium aluminium tetrahydride; In tetrahydrofuran; at 25 ℃; for 12h; Further stages.;

DOI:10.1021/jo020155k

upstream raw materials:

(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

(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

(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

cis-2,2-dimethyl-3a,7a-dihydrobenzo[1,3]dioxole

Downstream raw materials:

acetic acid 2,4-diacetoxy-7-hydroxy-6-oxo-2,3,4,4a,5,6-hexahydro[1,3]dioxolo[4,5-j]phenanthridin-3-yl ester

2,3,4,7-tetra-O-acetylnarciclasine

2,3,4,7-tetraacetoxy-cis-dihydronarciclasine

2,3,4,7-tetraacetoxy-trans-dihydronarciclasine

Refernces

• 1、 Bingham, Tanner W.,Hernandez, Lucas W.,Olson, Daniel G.,Svec, Riley L.,Hergenrother, Paul J.,Sarlah, David. "Enantioselective Synthesis of Isocarbostyril Alkaloids and Analogs Using Catalytic Dearomative Functionalization of Benzene". . p. 657 - 670. Retrieved 2019/01/08.
• 2、 Elango, Shanmugham,Yan, Tu-Hsin. "A short synthesis of (+)-narciclasine via a strategy derived from stereocontrolled epoxide formation and SnCl4-catalyzed arene-epoxide coupling". . p. 6954 - 6959. Retrieved 2007/10/03.