23095-44-5

Basic information

• Product Name: girinimbine
• Synonyms: girinimbine;3,11-Dihydro-3,3,5-trimethylpyrano[3,2-a]carbazole
• CAS NO: 23095-44-5
• Molecular Formula: C₁₈H₁₇NO
• Molecular Weight: 263.33
• Mol File: 23095-44-5.mol
• Article Data: 13

Chemical Properties

• Melting Point: 176 °C
• Boiling Point: 450°Cat760mmHg
• Flash Point: 161.5°C
• Appearance: /
• Density: 1.187g/cm³
• Vapor Pressure: 7.27E-08mmHg at 25°C
• Refractive Index: 1.68
• PKA: 17.31±0.40(Predicted)
• CAS DataBase Reference: girinimbine(CAS DataBase Reference)
• NIST Chemistry Reference: girinimbine(23095-44-5)
• EPA Substance Registry System: girinimbine(23095-44-5)

Safety Data

• Hazardous Substances Data: 23095-44-5(Hazardous Substances Data)

Usage

Definition

ChEBI: A natural product found in Clausena harmandiana.

InChI:InChI=1/C18H17NO/c1-11-10-14-12-6-4-5-7-15(12)19-16(14)13-8-9-18(2,3)20-17(11)13/h4-10,19H,1-3H3

Upstream product

• 113425-52-8 3,3-Dimethyl-1-oxo-1,2,3,11-tetrahydro-4-oxa-11-aza-benzo[a]fluorene-5-carboxylic acid methyl ester 
• 3350-78-5 3,3-Dimethylacryloyl chloride 
• 99-55-8 2-methyl-5-nitroaniline 
• 184896-34-2 1-methyl-2-[(2-methylbut-3-yn-2-yl)oxy]-4-nitrobenzene 
• 184896-36-4 2,2,8-trimethyl-5-nitro-2H-chromene 
• 5428-54-6 2-methyl-5-nitrophenol 
• 184896-30-8 5-amino-2,2,8-trimethylchromene 
• 113425-55-1 3-carbomethoxypyranocarbazole 
• 26870-54-2 2-hydroxy-3-methyl-carbazole-1-carbaldehyde 
• 4303-59-7 2-methylallyltriphenylphosphonium chloride 
• 113425-54-0 3,3-Dimethyl-1-(toluene-4-sulfonyloxy)-1,2,3,11-tetrahydro-4-oxa-11-aza-benzo[a]fluorene-5-carboxylic acid methyl ester 
• 113425-53-9 1-Hydroxy-3,3-dimethyl-1,2,3,11-tetrahydro-4-oxa-11-aza-benzo[a]fluorene-5-carboxylic acid methyl ester 
• 113425-51-7 3,3-Dimethyl-1-oxo-1,2,3,11-tetrahydro-4-oxa-11-aza-benzo[a]fluorene-5-carboxylic acid 
• 113425-50-6 2-(3-Methyl-but-2-enoyloxy)-9H-carbazole-3-carboxylic acid 

Downstream Products

• 161068-68-4 murranimbine 
• 161068-68-4 murranimbine 
• 27300-29-4 3',3'-dimethylpyrano[3,2-a]carbazole-3-carbaldehyde 

Relevant articles and documents

Pd-Catalyzed Formal [3 + 3] Heteroannulation of Allylic gem-Diacetates: Synthesis of Chromene-Based Natural Products and Exploration of Photochromic Properties

Palladium-catalyzed allylic alkylation reactions of allylic gem-diacetates are rarely explored. This work unveils an unusual chemical reactivity pattern of allylic gem-diacetates and establishes them as new prototypes to synthesize complex benzo[f]chromene systems. Under the reaction conditions, the diacetates behave as 1,3-dicationic equivalents and undergo a [3 + 3] heteroannulation with 2-naphthols (and meta-substituted phenols) to produce novel polycyclic chromenes possessing spiro-, tri-, and tetrasubstituted carbon centers. The versatility of the method is demonstrated in the synthesis of several chromene-based bioactive natural products. Further, interesting photochromic properties of the new classes of benzo[f]chromenes are also discovered.

Divergent and Orthogonal Approach to Carbazoles and Pyridoindoles from Oxindoles via Indole Intermediates

The previously unexplored Grignard addition to oxindoles provides a regiospecific approach to 2- and 2,3-disubstituted indole derivatives in high yields via a one-pot aromatization driven dehydration pathway. This method allows a convenient preparation of diallyl indoles that are used as ring-closing metathesis (RCM) precursors for the orthogonal synthesis of pyrido[1,2-a]indoles and carbazoles. The synthetic utility of this method is illustrated by the synthesis of a microtubulin inhibitor and naturally occurring carbazole alkaloids.

Pyrano[3,2-a]carbazole alkaloids as effective agents against ischemic stroke in vitro and in vivo

A series of pyrano[3,2-a]carbazole alkaloids were designed and synthesized as analogues of Claulansine F (Clau F, 10a) isolated from Clausena lansium. Some of compounds showed strong neuroprotective effects and were promising agents against ischemic stroke. Among these compounds, 7c was the most active in inhibiting the programmed death of PC12 cells and primary cortical neurons. This compound induced neuroprotection following ischemic reperfusion and decreased neurological deficit scores in treated animals. Furthermore, 7c could penetrate the blood-brain barrier (BBB) in rats, and its exposure in the brain was 4.3-fold higher than that in plasma. More importantly, compared to edaravone, 7c exhibited stronger free radical scavenging activity. Our findings suggest that 7c may be promising for further evaluation as an intervention for ischemic stroke.