Vincaminol

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Vincaminol
Vincaminol.svg
Names
IUPAC name
14α-(Hydroxymethyl)-14,15-dihydro-3α,16α-eburnamenin-14β-ol
Systematic IUPAC name
(41S,12S,13aS)-13a-Ethyl-12-(hydroxymethyl)-2,3,41,5,6,12,13,13a-octahydro-1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridin-12-ol
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C20H26N2O2/c1-2-19-9-5-10-21-11-8-15-14-6-3-4-7-16(14)22(17(15)18(19)21)20(24,12-19)13-23/h3-4,6-7,18,23-24H,2,5,8-13H2,1H3/t18-,19+,20+/m1/s1
    Key: YCXHPBHFOLIYEB-AABGKKOBSA-N
  • InChI=1/C20H26N2O2/c1-2-19-9-5-10-21-11-8-15-14-6-3-4-7-16(14)22(17(15)18(19)21)20(24,12-19)13-23/h3-4,6-7,18,23-24H,2,5,8-13H2,1H3/t18-,19+,20+/m1/s1
    Key: YCXHPBHFOLIYEB-AABGKKOBBO
  • CC[C@@]12CCCN3[C@@H]1c4c(c5ccccc5n4[C@](C2)(CO)O)CC3
Properties
C20H26N2O2
Molar mass 326.440 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Vincaminol (C20H26N2O2) is a chemical that is a part of the Vinca alkaloid group, which were discovered in the 1950s by a Canadian scientist and are derived from Vinca minor (periwinkle). [1] [2] Vincaminol is not as well known as some of the other Vinca alkaloids such as vinblastine, vinorelbine, vincristine, and vindesine, which are the four main, medically useful Vinca alkaloids.

Uses

Vincaminol is used in to synthesize vincamine.[ citation needed ]

Related Research Articles

<span class="mw-page-title-main">Alkaloid</span>

Bansal, Raj K. (2003). A Textbook of Organic Chemistry. New Age International Limited. p. 644. ISBN 978-81-224-1459-2.

<span class="mw-page-title-main">Apocynaceae</span> Dogbane and oleander family of flowering plants

Apocynaceae is a family of flowering plants that includes trees, shrubs, herbs, stem succulents, and vines, commonly known as the dogbane family, because some taxa were used as dog poison. Members of the family are native to the European, Asian, African, Australian, and American tropics or subtropics, with some temperate members. The former family Asclepiadaceae is considered a subfamily of Apocynaceae and contains 348 genera. A list of Apocynaceae genera may be found here.

<i>Catharanthus</i> Genus of flowering plants

Catharanthus is a genus of flowering plants in the family Apocynaceae. Like the genus Vinca, they are known commonly as periwinkles. There are eight known species. Seven are endemic to Madagascar, though one, C. roseus, is widely naturalized around the world. The eighth species, C. pusillus, is native to India and Sri Lanka. The name Catharanthus comes from the Greek for "pure flower".

<span class="mw-page-title-main">Laboratoires Pierre Fabre</span>

Laboratoires Pierre Fabre is a French multinational pharmaceutical and cosmetics company. The company had a consolidated turnover of 1.978 billion euros in 2012. It is headquartered in the city of Castres, Midi-Pyrénées, France.

<i>Vinca</i> Genus of flowering plants

Vinca is a genus of flowering plants in the family Apocynaceae, native to Europe, northwest Africa and southwest Asia. The English name periwinkle is shared with the related genus Catharanthus.

<span class="mw-page-title-main">Vinorelbine</span> Pharmaceutical drug

Vinorelbine (NVB), sold under the brand name Navelbine among others, is a chemotherapy medication used to treat a number of types of cancer. This includes breast cancer and non-small cell lung cancer. It is given by injection into a vein or by mouth.

<i>Catharanthus roseus</i> Species of flowering plant in the family Apocynaceae

Catharanthus roseus, commonly known as bright eyes, Cape periwinkle, graveyard plant, Madagascar periwinkle, old maid, pink periwinkle, rose periwinkle, is a perennial species of flowering plant in the family Apocynaceae. It is native and endemic to Madagascar, but is grown elsewhere as an ornamental and medicinal plant, and now has a pantropical distribution. It is a source of the drugs vincristine and vinblastine, used to treat cancer. It was formerly included in the genus Vinca as Vinca rosea.

<i>Vinca minor</i> Species of flowering plant in the dogbane family

Vinca minor is a species of flowering plant in the dogbane family, native to central and southern Europe, from Portugal and France north to the Netherlands and the Baltic States, east to the Caucasus, and also southwestern Asia in Turkey. Other vernacular names used in cultivation include small periwinkle, common periwinkle, and sometimes in the United States, myrtle or creeping myrtle.

<span class="mw-page-title-main">Rescinnamine</span> Chemical compound

Rescinnamine, known by the brand names Moderil, Cinnasil, and Anaprel, is an angiotensin-converting enzyme inhibitor used as an antihypertensive drug.

<i>Vinca</i> alkaloid

Vinca alkaloids are a set of anti-mitotic and anti-microtubule alkaloid agents originally derived from the periwinkle plant Catharanthus roseus and other vinca plants. They block beta-tubulin polymerization in a dividing cell.

<span class="mw-page-title-main">Vindesine</span> Chemical compound

Vindesine, also termed Eldisine, is a semisynthetic vinca alkaloid derived from the flowering plant Catharanthus roseus. Like the natural and semisynthetic vinca alkaloids derived from this plant, vindesine is an inhibitor of mitosis that is used as a chemotherapy drug. By inhibiting mitosis, vinedsine blocks the proliferation of cells, particularly the rapidly proliferation cells of certain types of cancer. It is used, generally in combination with other chemotherapeutic drugs, in the treatment of various malignancies such as leukaemia, lymphoma, melanoma, breast cancer, and lung cancer.

<span class="mw-page-title-main">Vincamine</span> Chemical compound

Vincamine is a monoterpenoid indole alkaloid found in the leaves of Vinca minor, comprising about 25–65% of its indole alkaloids by weight. It can also be synthesized from related alkaloids.

<span class="mw-page-title-main">Mitotic inhibitor</span> Cell division inhibitor

A mitotic inhibitor, microtubule inhibitor, or tubulin inhibitor, is a drug that inhibits mitosis, or cell division, and is used in treating cancer, gout, and nail fungus. These drugs disrupt microtubules, which are structures that pull the chromosomes apart when a cell divides. Mitotic inhibitors are used in cancer treatment, because cancer cells are able to grow through continuous division that eventually spread through the body (metastasize). Thus, cancer cells are more sensitive to inhibition of mitosis than normal cells. Mitotic inhibitors are also used in cytogenetics, where they stop cell division at a stage where chromosomes can be easily examined.

<span class="mw-page-title-main">Akuammine</span> Chemical compound

Akuammine (vincamajoridine) is an indole alkaloid. It is the most abundant alkaloid found in the seeds from the tree Picralima nitida, commonly known as akuamma, comprising 0.56% of the dried powder. It has also been isolated from Vinca major. Akuammine is structurally related to yohimbine, mitragynine and more distantly Voacangine, all of which are alkaloid plant products with pharmacological properties.

<span class="mw-page-title-main">Vinflunine</span> Chemical compound

Vinflunine is a novel fluorinated vinca alkaloid derivative undergoing research for the treatment of bladder cancer. It was originally discovered by the team of the Professor Jean-Claude Jacquesy, developed by Laboratoires Pierre Fabre and was licensed to Bristol-Myers Squibb for development in certain countries, including the United States.

<span class="mw-page-title-main">Vinburnine</span> Chemical compound

Vinburnine is a vasodilator. Vincamone is a vinca alkaloid and a metabolite of vincamine.

Keller's reagent can refer to either of two different mixtures of acids.

<span class="mw-page-title-main">Akuammicine</span> Alkaloid

Akuammicine is a monoterpene indole alkaloid of the Vinca sub-group. It is found in the Apocynaceae family of plants including Picralima nitida, Vinca minor and the Aspidosperma.

"7+3" in the context of chemotherapy is an acronym for a chemotherapy regimen that is most often used today as first-line induction therapy in acute myelogenous leukemia, excluding the acute promyelocytic leukemia form, which is better treated with ATRA and/or arsenic trioxide and requires less chemotherapy.

<span class="mw-page-title-main">Vinervine</span> Vinca alkaloid

Vinervine is a monoterpene indole alkaloid of the Vinca sub-group. It is a derivative of akuammicine, with one additional hydroxy (OH) group in the indole portion, hence it is also known as 12-hydroxyakuammicine.

References

  1. PubChem. "Vincaminol". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-11-15.
  2. Smeyers, Yves G.; Smeyers, Nadine J.; Randez, Juan J.; Hernandez-Laguna, A.; Galvez-Ruano, E. (1991-06-01). "A structural and pharmacological study of alkaloids of Vinca Minor". Molecular Engineering. 1 (2): 153–160. doi:10.1007/BF00420051. ISSN   1572-8951. S2CID   93210480.