2632-29-3

Basic information

• Product Name: tubulosine
• Synonyms: tubulosine;10,11-Dimethoxytubulosan-8'-ol
• CAS NO: 2632-29-3
• Molecular Formula: C₂₉H₃₇N₃O₃
• Molecular Weight: 475.62238
• Mol File: 2632-29-3.mol

Chemical Properties

• Melting Point: 282-283 °C
• Boiling Point: 667.8°Cat760mmHg
• Flash Point: 357.7°C
• Appearance: /
• Density: 1.27g/cm³
• PKA: 9.78±0.40(Predicted)
• CAS DataBase Reference: tubulosine(CAS DataBase Reference)
• NIST Chemistry Reference: tubulosine(2632-29-3)
• EPA Substance Registry System: tubulosine(2632-29-3)

Safety Data

• Hazardous Substances Data: 2632-29-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Tubulosine is used as a potential therapeutic agent for the treatment of various diseases, including cancer. Its unique chemical structure and functional groups allow it to interact with cellular targets and modulate biological pathways, making it a promising candidate for drug development.
Used in Chemical Research:
Tubulosine is also used as a subject of study in chemical research, particularly in the field of natural products chemistry and alkaloid chemistry. Its unique properties and structural features provide valuable insights into the development of new compounds and understanding their biological activities.
Used in Drug Discovery:
Tubulosine can be employed as a lead compound in drug discovery processes, where its chemical structure can be modified and optimized to enhance its therapeutic potential and selectivity towards specific targets. This can lead to the development of novel drugs with improved efficacy and safety profiles.

References

Brauchli et al., 1. Amer. Chem. Soc., 86, 1895 (1964)

Upstream product

• 3851-29-4 2,3-(R,R)-11b-(S)-(3-ethyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-α]isoquinoline-2-yl)acetic acid methyl ester 
• 21197-07-9 2,3-(R,R)-11b-(S)-N-[2-(5-benzyloxy-1H-indol-3-yl)-ethyl]-2-(3-ethyl-9,10-dimethoxy-1,3,4,6,7,7a,11a,11b-octahydro-2H-pyrido[2,1-α]isoquinolin-2-yl)acetamide 
• 20776-45-8 5-benzyloxytryptamine 
• 31248-76-7 2,3-(R,R)-11b-(S)-O-benzyl-dehydrotubulosine 
• 30833-25-1 O-benzyltubulosine 

Relevant articles and documents

Two alangium alkaloids from Alangium lamarckii

Two new Alangium alkaloids, 1',2'-dehydrotubulosine (1) and alangine (2), were isolated from the dried fruits of Alangium lamarckii along with tubulosine (3), isotubulosine (4), deoxytubulosine, cephaeline, isocephaeline, psychotrine, neocephaeline, 10-O-

Enantioselective total syntheses of the Ipecacuanha alkaloid emetine, the Alangium alkaloid tubulosine and a novel benzoqainolizidine alkaloid by using a domino process

The first enantioselective syntheses of the Ipecacuanha alkaloid emetine (1) and the Alangium alkaloid tubulosine (2) is described employing a domino Knoevenagel/hetero-Diels-Alder reaction and an enantioselective catalytic transfer hydrogenation of imines as key steps. Thus, hydrogenation of the imine 15 with the catalyst (R,R)-16 gives the tetrahydroisoquinoline 14 with 95% ee which was transformed into the aldehyde (1S)-7. The three-component domino reaction of (1S)-7 with 6 and 8 led to 19, which in a second domino process was treated with K2CO3 in methanol followed by a hydrogenation to give the benzoquinolizidine 4 together with the diastereomers 22 and 23 in a overall yield of 66%. Further transformation of 4 with the amines 3 and 5 yielded enantiopure emetine (1) and tubulosine (2), respectively. In addition, starting from 19 the novel benzoquinolizidine alkaloid 34 was synthesised; this compound resembles the vallesiachotamine alkaloid dihydroantirhin 31, which has not been isolated so far but probably must also exist in nature.