6271-21-2

Basic information

• Product Name: dihydrolycorine
• Synonyms: (1S,2S,3aR,12bS,12cR)-2,3,3a,4,5,7,12b,12c-Octahydro-1H-[1,3]dioxolo[4,5-j]pyrrolo[3,2,1-de]phenanthridine-1,2-diol
• CAS NO: 6271-21-2
• Molecular Formula: C16H19NO4
• Molecular Weight: 289.329
• Mol File: 6271-21-2.mol
• Article Data: 3

Chemical Properties

• Melting Point: 247 °C
• Boiling Point: 460.5 °C at 760 mmHg
• Flash Point: 232.3 °C
• Appearance: /
• Density: 1.48
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.701
• PKA: 14.13±0.40(Predicted)
• CAS DataBase Reference: dihydrolycorine(CAS DataBase Reference)
• NIST Chemistry Reference: dihydrolycorine(6271-21-2)
• EPA Substance Registry System: dihydrolycorine(6271-21-2)

Safety Data

• Hazardous Substances Data: 6271-21-2(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 6271-21-2 differently. You can refer to the following data:
1. Dihydrolycorine is a derivative of Lycorine, the main phenanthridine Amaryllidaceae alkaloid which exhibits significant antitumor activity in cancer cells that display resistance to proapoptotic stimuli.
2. Dihydrolycorine is a derivative of Lycorine (L487550), the main phenanthridine Amaryllidaceae alkaloid which exhibits significant antitumor activity in cancer cells that display resistance to proapoptotic stimuli.

Description

Dihydrolycorine is a derivative of the alkaloid lycorine that has antihypertensive and neuroprotective activities. It inhibits methoxamine-induced contraction of isolated rabbit aortic rings and rat anococcygeus muscle with pA2 values of 5.93 and 6.35, respectively. Dihydrolycorine reduces mean arterial pressure (MAP) in anesthetized and conscious normotensive rats when administered at a dose of 80 mg/kg. It also reduces electrically or phenylephrine-induced hypertension in pithed rats. Dihydrolycorine reduces infarct size, cerebral edema, and myeloperoxidase activity in a rat model of focal cerebral ischemia-reperfusion injury when administered following reperfusion.

InChI:InChI=1/C16H19NO4/c18-11-3-8-1-2-17-6-9-4-12-13(21-7-20-12)5-10(9)14(15(8)17)16(11)19/h4-5,8,11,14-16,18-19H,1-3,6-7H2/t8-,11+,14+,15-,16-/m1/s1

Upstream product

• 58700-89-3 (1α,2β)-1,2-dihydroxy-9,10-[methylenebis(oxy)]galanthan-7-one 
• 58700-83-7 4t-(2-chloro-ethyl)-(4ar,11bt)-3,4a,5,11b-tetrahydro-4H-[1,3]dioxolo[4,5-j]phenanthridin-6-one 
• 58700-82-6 4t-(2-hydroxy-ethyl)-(4ar,11bt)-3,4a,5,11b-tetrahydro-4H-[1,3]dioxolo[4,5-j]phenanthridin-6-one 
• 58700-85-9 rac-9,10-methanediyldioxy-galanth-1-ene-5,7-dione 
• 58700-87-1 rac-9,10-methanediyldioxy-galanth-1-en-7-one 
• 66409-92-5 6-oxo-(4ar,11bt)-3,4,4a,5,6,11b-hexahydro-[1,3]dioxolo[4,5-j]phenanthridine-4t-carboxylic acid 
• 42390-68-1 methyl 2c-(N-methoxycarbonylamino)-3t-(3,4-methylenedioxyphenyl)cyclohex-4-enyl-r-acetate 
• 58700-81-5 (6-oxo-(4ar,11bt)-3,4,4a,5,6,11b-hexahydro-[1,3]dioxolo[4,5-j]phenanthridin-4t-yl)-acetic acid methyl ester 
• 2030-56-0 rac-1α,2α-diacetoxy-9,10-methanediyldioxy-galanthan-7-one 
• 58700-84-8 (6-oxo-(4ar,11bc)-3,4,4a,5,6,11b-hexahydro-[1,3]dioxolo[4,5-j]phenanthridin-4t-yl)-acetic acid 
• 58700-84-8 (6-oxo-(4ar,11bt)-3,4,4a,5,6,11b-hexahydro-[1,3]dioxolo[4,5-j]phenanthridin-4t-yl)-acetic acid 
• 58700-94-0 1α,2α-epoxy-9,10-methanediyldioxy-galanthan-7-one 
• 30074-38-5 rac-2β-acetoxy-1α-iodo-9,10-methanediyldioxy-(15α)-galanthane-5,7-dione 
• 30074-37-4 1c-iodo-(6ac,13bc)-1,5,6,6a,7,13b-hexahydro-2H-2r,6c-methano-[1,3]dioxolo[4,5-g]oxocino[5,4-c]isoquinoline-4,8-dione 

Relevant articles and documents

Synthesis and antiviral activity of lycorine derivatives

There are no effective antiviral drugs to treat hand, foot, and mouth disease. In this study, a series of lycorine derivatives were synthesized and evaluated against enterovirus 71 and coxsackievirus A16 in?vitro. Derivatives 7c-m with the phenoxyacyl gro

LYCORINE STRUCTURE-ACTIVITY RELATIONSHIPS

Twenty three lycorine derivatives and naturally occurring alkaloids, structurally related to lycorine, were tested for their ability to inhibit ascorbic acid biosynthesis in potato tubers.The following relationships between structure modification and activity were observed: (a) cleavage of the acetalic bonds on the dioxole ring had no effect on activity; (b) derivatives with a methoxy group on C-8 (A ring) were inactive; (c) oxidation of NCH2-7 to an amide group (B ring) caused loss of activity; (d) modification of the C/D ring junction had no effect on activity when the D ring assumed a β configuration whereas a great deciease of activity was observed when that ring assumed an α configuration; (e) selective or complete acetylation of hydroxyl groups of the C ring, epimerization or oxidation of the hydroxyl group on C-2 led to a loss of activity; (f) a compound with a double bond located in the 1,2-position showed activity almost identical to lycorine; (g) stereoselective hydrogenation of the double bond of the C ring induced a considerable increase of the activity; (h) protonation of the nitrogen atom had no effect on activity.Key Word Index- Sternbergia lutea; Amaryllidaceae; alkaloids; lycorine; lycorine derivatives; structure-activity relationships; ascorbate biosynthesis inhibition.