116664-93-8

Basic information

• Product Name: sampangine
• Synonyms: sampangine
• CAS NO: 116664-93-8
• Molecular Formula: C₁₅H₈N₂O
• Molecular Weight: 232.2368
• Mol File: 116664-93-8.mol

Chemical Properties

• Boiling Point: 498.2°Cat760mmHg
• Flash Point: 251.5°C
• Appearance: /
• Density: 1.404g/cm³
• Vapor Pressure: 1.67E-08mmHg at 25°C
• Refractive Index: 1.757
• CAS DataBase Reference: sampangine(CAS DataBase Reference)
• NIST Chemistry Reference: sampangine(116664-93-8)
• EPA Substance Registry System: sampangine(116664-93-8)

Safety Data

• Hazardous Substances Data: 116664-93-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C15H10N2O/c18-15-11-4-2-1-3-10(11)13-12-9(5-7-16-13)6-8-17-14(12)15/h1-8,12,14H

Upstream product

• 92599-17-2 4-methyl-5,6-dihydrobenzoquinoline-5,6-dione 
• 1188-33-6 N,N-dimethylformamide diethyl diacetal 
• 161237-41-8 sampangine 6-N-oxide 
• 374538-03-1 2-methoxycarbonylphenylboronic acid 
• 2065-37-4 2-bromo-1,4-naphthoquinone 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 96889-94-0 cleistopholine 

Relevant articles and documents

Synthesis of the azaoxoaporphine alkaloid sampangine and ascididemin-type pyridoacridines through TMPMgCl·LiCl-mediated ring closure

We report the synthesis of the azaoxoaporphine alkaloid sampangine (4) and a series of ring A analogues and isomers of the marine pyridoacridine alkaloid ascididemin (2). This approach starts from readily available 1-bromo[2,7]naphthyridine (12) or 4-bromobenzo[c][2,7]naphthyridine (5), and the ring A scaffold bearing an ester moiety is introduced by a Suzuki or Negishi cross-coupling reaction. The final cyclization step was achieved through a directed remote ring metallation with the Knochel-Hauser base (TMPMgCl·LiCl; TMP = 2,2,6,6-tetramethylpiperidinyl), followed by intramolecular trapping of the ester group.

Synthesis of eupomatidines 1, 2 and 3 and related compounds including iminoquinolinequinone structure

Three aromatic alkaloids, eupomatidines 1 (1), 2 (2), and 3 (3), and two elated compounds (27, 28) were synthesized from (6-methoxy-)1,4-naphthoquinone by hetero Diels-Alder reaction with (2-methoxy-)2-butenal dimethylhydrazone.

4- Substituted sampangine derivatives: Novel acetylcholinesterase and β-myloid aggregation inhibitors

A series of 4- substituted sampangine derivatives (4-aminoalkylaminosampangine Ar–NH(CH2)nNR1R2) has been designed, synthesized, and tested for their ability to inhibit acetylcholinesterase (AChE), butyrylcholinesterase (BChE) and β-myloid (Aβ) aggregation. The synthetic compounds exhibited high AChE inhibitory activity and a significant in vitro inhibitory potency toward the self-induced Aβ aggregation. While, treatment of SH-SY5Y cells overexpressing the Swedish mutant form of human β-amyloid precursor protein (APPsw) with derivatives was associated with significant reduction of Aβ42 secretion levels. Moreover, most of the synthetic compounds were predicted to be able to cross the blood-brain barrier (BBB) to reach their targets in the central nervous system (CNS) according to a parallel artificial membrane permeation assay for BBB. The result encourages us to study this class of compounds thoroughly and systematically.

Synthetic studies of imbiline 1, a constituent of Eupomatia species

Imbiline 1 (1a), a constituent of Eupomatia species, was synthesized from 4-methoxy-1-naphthylamine hydrochloride (8) in seven steps. A reaction of aldehydes and methyl methylthiomethyl sulfoxide was also studied.

4-substituted Sampangine alkaloid derivative as well as synthesis method and application thereof

The invention discloses a 4-substituted Sampangine alkaloid derivative as well as a synthesis method and application thereof. The 4-substituted Sampangine alkaloid derivative is of a structure as shown in the following formula (I). The synthesis method comprises the following steps: putting Sampangine alkaloid which is of a structure as shown in the formula (II) and perbrominated pyridine bromide into a first organic solvent for reaction, thus obtaining 4-bromo-substituted Sampangine alkaloid which is of a structure as shown in the formula (III), then carrying out a reaction between the 4-bromo-substituted Sampangine alkaloid and sodium methylate in a second organic solvent, thus obtaining 4-methoxy substituted Sampangine alkaloid which is of a structure as shown in the formula (IV), and then carrying out reaction on the 4-methoxy substituted Sampangine alkaloid and diamine which is of a structure as shown in the formula (V) in a third organic solvent, thus obtaining a corresponding target compound coarse product. The compounds which are of the structures as shown in the formulas from (I) to (V) are as follows: as shown in the specification, wherein in the formula (I) and the formula (V), n is equal to a value ranging from 2 to 3, R2 is -N(CH3)3, -NEt2, -OH, a compound shown in the specification or a compound shown in the specification.

Fungicidal properties of sampangine and its analogs to agriculturally important fungal plant pathogens

It has been found that sampangine and related analogs such as benzo[4,5]sampangine, 4-bromosampangine and 4-methoxysampangine may be used as effective fungicidal agents for plants. Fungicidal plant compositions and methods of using the materials for such

Copyrine alkaloids: Synthesis, spectroscopic characterization, and antimycotic/antimycobacterial activity of A- and B-ring-functionalized sampangines

Several A- and B-ring-substituted sampangines were synthesized and evaluated for antifungal and antimycobacterial activity against AIDS-related opportunistic infection pathogens. Electrophilic halogenation provided a channel for structural elaboration of

Polycyclic Aromatic Alkaloids, I. - Synthesis of Cleistopholine and Sampangine

Cleistopholine (4) is prepared in one-pot synthesis by Diels-Alder cycloaddition of 1 to 2, followed by thermal elimination of dimethylamine.Reaction of 4 with tripiperidinomethane or dimethylformamide diethyl acetal yields the enamines 5a/5b, which, without further purification, give sampangine (6) on heating with ammonium chloride in glacial acetic acid.