509-15-9 | Gelsemine

Packsize	Purity	Availability	Price	Discounted Price
5mg	95%	in stock	$120.00	$84.00
10mg	95%	in stock	$172.00	$120.00
100mg	95%	in stock	$1,646.00	$1,152.00

Description

• Catalog Number: AG19471
• Chemical Name: Gelsemine
• CAS Number: 509-15-9
• Molecular Formula: C20H22N2O2
• Molecular Weight: 322.4009
• MDL Number: MFCD00082347
• SMILES: C=CC12CN([C@H]3[C@@H]2[C@]2([C@H]4C[C@@H]1C3CO4)C(=O)Nc1c2cccc1)C

Computed Properties

• Complexity: 635
• Covalently-Bonded Unit Count: 1
• Defined Atom Stereocenter Count: 7
• Heavy Atom Count: 24
• Hydrogen Bond Acceptor Count: 3
• Hydrogen Bond Donor Count: 1
• Rotatable Bond Count: 1
• XLogP3: 1.8

Literature

• Biomimetic total synthesis of (+)-gelsemine.

  Angewandte Chemie (International ed. in English) 20120514

• Nectar alkaloids decrease pollination and female reproduction in a native plant.

  Oecologia 20120401

• [Study on anti-proliferation activity and the mechanisms of alkaloid monomers from Gelsemium elegans on HepG2 cell in vitro].

  Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20120301

• Preparative separation of alkaloids from Gelsemium elegans Benth. using pH-zone-refining counter-current chromatography.

  Journal of chromatography. A 20110610

• Antitumor activity of two gelsemine metabolites in rat liver microsomes.

  Journal of Asian natural products research 20100901

• A concise approach to a gelsemine core structure using an oxygen to carbon bridge swapping strategy.

  Organic letters 20081106

• Regulation of neurosteroid allopregnanolone biosynthesis in the rat spinal cord by glycine and the alkaloidal analogs strychnine and gelsemine.

  Neuroscience 20080422

• Double conjugate addition of a nitropropionate ester to a quinone monoketal: synthesis of an advanced intermediate to (+/-)-gelsemine.

  Organic letters 20070802

• Pattern recognition in retrosynthetic analysis: snapshots in total synthesis.

  The Journal of organic chemistry 20070608

• Isolation of gelsedine-type indole alkaloids from Gelsemium elegans and evaluation of the cytotoxic activity of gelsemium alkaloids for A431 epidermoid carcinoma cells.

  Journal of natural products 20060401

• Aza-cope rearrangement-mannich cyclizations for the formation of complex tricyclic amines: stereocontrolled total synthesis of (+/-)-gelsemine.

  Journal of the American Chemical Society 20051228

• Use of the intramolecular Heck reaction for forming congested quaternary carbon stereocenters. Stereocontrolled total synthesis of (+/-)-gelsemine.

  Journal of the American Chemical Society 20051228

• Modeling the stereoselectivity of the Johnson-Claisen rearrangements in the Danishefsky synthesis of gelsemine.

  The Journal of organic chemistry 20050902

• A convenient one-pot procedure to afford bicyclic molecules by stereospecific iron carbonyl mediated [6 + 2] ene-type cyclization: a possible approach to gelsemine.

  Journal of the American Chemical Society 20031105

• Gelsemine: a thought-provoking target for total synthesis.

  Angewandte Chemie (International ed. in English) 20030103

• Explorations in organic chemistry leading to the total synthesis of (+/-)-gelsemine.

  Journal of the American Chemical Society 20020821

• Indole synthesis by radical cyclization of o-alkenylphenyl isocyanides and its application to the total synthesis of natural products.

  Chemical record (New York, N.Y.) 20020101