Manzamine A

Base Information

• Chemical Name: Manzamine A
• CAS No.: 104196-68-1
• Molecular Formula: C₃₆H₄₄N₄O
• Molecular Weight: 548.772
• DSSTox Substance ID: DTXSID001098329
• Wikidata: Q27135285
• Metabolomics Workbench ID: 64730
• ChEMBL ID: CHEMBL326531,CHEMBL403233
• Mol file: 104196-68-1.mol

Synonyms:manzamine A

Chemical Property of Manzamine A

Chemical Property:

• Vapor Pressure: 4.65E-24mmHg at 25°C
• Boiling Point: 756.6°Cat760mmHg
• PKA: 13.58±0.40(Predicted)
• Flash Point: 411.4°C
• PSA: 55.39000
• Density: 1.26g/cm³
• LogP: 6.73160
• Storage Temp.: -20°
• Solubility.: Soluble in DMSO (up to 25 mg/ml).
• XLogP3: 5.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 548.35151204
• Heavy Atom Count: 41
• Complexity: 1050

Purity/Quality:

98%Min ^*data from raw suppliers

ManzamineA ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCN2CCC3C(=CC(CCC=CC1)(C4C3(C2)CC5N4CCCCC=C5)O)C6=NC=CC7=C6NC8=CC=CC=C78
• Isomeric SMILES: C1CCN2CC[C@H]3C(=C[C@@](CC/C=C\C1)([C@H]4[C@]3(C2)C[C@H]/5N4CCCC/C=C5)O)C6=NC=CC7=C6NC8=CC=CC=C78
• Description: Manzamine A (104196-68-1) inhibits vacuolar ATPases and inhibits autophagy in pancreatic cancer cells1. Suppresses atherosclerosis?in vivo2. Manzamine A displays neuritogenic activity3?and suppresses tau hyperphosphorylation in human neuroblastoma cell lines4.
• Uses: Manzamine A is a β-Carboline alkaloid with anti-inflammatory.

Technology Process of Manzamine A

There total 41 articles about Manzamine A 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: 50.0%

Manzamine D (116477-23-7) → manzamine A (104196-68-1)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone;

DOI:10.1021/ja981303k

Reference yield:

C30H46N2O4 → manzamine A (104196-68-1)

Guidance literature:

Multi-step reaction with 16 steps

1: C₅H₅N, AcOH

3: LHMDS

4: NaBH₄

5: Et₃N

6: DBU / benzene / Heating

7: 1.) m-CPBA, 2.) NaOMe

8: TBAF

9: Et₃N

10: TFA

11: 89 percent / (iPr)2NEt

12: 94 percent / H₂ / Lindlar catalyst

13: 83 percent / DIBAL-H

14: 90 percent / Dess-Martin reagent

15: 58 percent / TFA

16: 50 percent / DDQ

With pyridine; sodium tetrahydroborate; tetrabutyl ammonium fluoride; hydrogen; sodium methylate; diisobutylaluminium hydride; Dess-Martin periodane; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; Lindlar's catalyst; In benzene;

DOI:10.1021/ja981303k

Reference yield:

5-[(Z)-(R)-1-((E)-12-Hydroxy-3-oxo-dodec-1-en-7-ynyl)-1,2,5,6,7,8-hexahydro-azocin-2-ylmethyl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester → manzamine A (104196-68-1)

Guidance literature:

Multi-step reaction with 17 steps

1: Irradiation

2: C₅H₅N, AcOH

4: LHMDS

5: NaBH₄

6: Et₃N

7: DBU / benzene / Heating

8: 1.) m-CPBA, 2.) NaOMe

9: TBAF

10: Et₃N

11: TFA

12: 89 percent / (iPr)2NEt

13: 94 percent / H₂ / Lindlar catalyst

14: 83 percent / DIBAL-H

15: 90 percent / Dess-Martin reagent

16: 58 percent / TFA

17: 50 percent / DDQ

With pyridine; sodium tetrahydroborate; tetrabutyl ammonium fluoride; hydrogen; sodium methylate; diisobutylaluminium hydride; Dess-Martin periodane; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; Lindlar's catalyst; In benzene;

DOI:10.1021/ja981303k

upstream raw materials:

Manzamine D

tryptamine

Ircinal A

Refernces

Stereoselective synthesis of the tricyclic core ABC-rings of nakadomarin and manzamine from a common intermediate

10.1016/S0040-4039(01)02301-2

The study focuses on the stereoselective synthesis of the tricyclic core ABC-rings of nakadomarin and manzamine, which are complex marine alkaloids with cytotoxic and antimicrobial properties. The researchers used a common intermediate and the Pauson–Khand cyclization reaction to construct the core structure. Key chemicals involved in the study include enamide 9, cyclopentenone 10, and nakadomarin 1. The Pauson–Khand reaction involved the use of Co2(CO)8 (cobalt carbonyl), n-BuSMe (n-butylthiomethyl ether), and various solvents such as trifluoroethanol and 1,2-dichloroethane. These chemicals served to facilitate the cyclization and subsequent reduction steps, ultimately leading to the formation of the desired tricyclic core structures, which are precursors to both nakadomarin and manzamine. The study also explored the stereochemistry of the products and attempted ring expansion reactions to further synthesize manzamine.

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