Vindorosine | CAS#5231-60-7 | inhibitor

MedKoo Cat#: 585391 | Name: Vindorosine

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Vindorosine is extracted from Catharanthus roseus, and reduces KCl-stimulated Ca(2+) influx in the smooth muscles of rat renal arteries.

Chemical Structure

Vindorosine

CAS#5231-60-7

Theoretical Analysis

MedKoo Cat#: 585391

Name: Vindorosine

CAS#: 5231-60-7

Chemical Formula: C24H30N2O5

Exact Mass: 426.2155

Molecular Weight: 426.51

Elemental Analysis: C, 67.59; H, 7.09; N, 6.57; O, 18.76

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

No Data

Synonym

Vindorosine

IUPAC/Chemical Name

methyl 11-acetyloxy-12-ethyl-10-hydroxy-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraene-10-carboxylate

InChi Key

SASWULSUPROHRT-UHFFFAOYSA-N

InChi Code

InChI=1S/C24H30N2O5/c1-5-22-11-8-13-26-14-12-23(18(22)26)16-9-6-7-10-17(16)25(3)19(23)24(29,21(28)30-4)20(22)31-15(2)27/h6-11,18-20,29H,5,12-14H2,1-4H3

SMILES Code

O=C(C1(O)C2N(C)C3=CC=CC=C3C(C45)2CCN5CC=CC4(CC)C1OC(C)=O)OC

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 426.51 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Chen W, Yang XD, Tan WY, Zhang XY, Liao XL, Zhang H. Total Synthesis of (-)-Vindorosine. Angew Chem Int Ed Engl. 2017 Sep 25;56(40):12327-12331. doi: 10.1002/anie.201707249. Epub 2017 Aug 24. PubMed PMID: 28782228. 2: Wu XL, Cheang WS, Zhang DM, Li Y, Lau CW, Wang GC, Huang Y, Ye WC. Antagonism of Ca2+ influx via L-type Ca2+ channels mediates the vasorelaxant effect of Catharanthus roseus-derived vindorosine in rat renal artery. Planta Med. 2014 Dec;80(18):1672-7. doi: 10.1055/s-0034-1383220. Epub 2014 Oct 23. PubMed PMID: 25340466. 3: Wang Y, Lin J, Wang X, Wang G, Zhang X, Yao B, Zhao Y, Yu P, Lin B, Liu Y, Cheng M. Brønsted Acid-Catalyzed Tandem Cyclizations of Tryptamine-Ynamides Yielding 1H-Pyrrolo[2,3-d]carbazole Derivatives. Chemistry. 2018 Mar 15;24(16):4026-4032. doi: 10.1002/chem.201705189. Epub 2018 Jan 10. PubMed PMID: 29168592. 4: Qu Y, Easson ML, Froese J, Simionescu R, Hudlicky T, De Luca V. Completion of the seven-step pathway from tabersonine to the anticancer drug precursor vindoline and its assembly in yeast. Proc Natl Acad Sci U S A. 2015 May 12;112(19):6224-9. doi: 10.1073/pnas.1501821112. Epub 2015 Apr 27. PubMed PMID: 25918424; PubMed Central PMCID: PMC4434687. 5: Sasaki Y, Kato D, Boger DL. Asymmetric total synthesis of vindorosine, vindoline, and key vinblastine analogues. J Am Chem Soc. 2010 Sep 29;132(38):13533-44. doi: 10.1021/ja106284s. PubMed PMID: 20809620; PubMed Central PMCID: PMC2944909. 6: Sears JE, Boger DL. Tandem Intramolecular Diels-Alder/1,3-Dipolar Cycloaddition Cascade of 1,3,4-Oxadiazoles: Initial Scope and Applications. Acc Chem Res. 2016 Feb 16;49(2):241-51. doi: 10.1021/acs.accounts.5b00510. Epub 2016 Jan 27. PubMed PMID: 26813287; PubMed Central PMCID: PMC4755904. 7: Elliott GI, Velcicky J, Ishikawa H, Li Y, Boger DL. Total synthesis of (-)- and ent-(+)-vindorosine: tandem intramolecular Diels-Alder/1,3-dipolar cycloaddition of 1,3,4-oxadiazoles. Angew Chem Int Ed Engl. 2006 Jan 16;45(4):620-2. PubMed PMID: 16355429. 8: Büchi G, Matsumoto KE, Nishimura H. The total synthesis of (plus or minus)-vindorosine. J Am Chem Soc. 1971 Jun 30;93(13):3299-301. PubMed PMID: 5559600. 9: Deluca V, Balsevich J, Tyler RT, Kurz WG. Characterization of a novel N-methyltransferase (NMT) from Catharanthus roseus plants : Detection of NMT and other enzymes of the indole alkaloid biosynthetic pathway in different cell suspension culture systems. Plant Cell Rep. 1987 Dec;6(6):458-61. doi: 10.1007/BF00272782. PubMed PMID: 24248932. 10: Matsuoka J, Kumagai H, Inuki S, Oishi S, Ohno H. Construction of the Pyrrolo[2,3-d]carbazole Core of Spiroindoline Alkaloids by Gold-Catalyzed Cascade Cyclization of Ynamide. J Org Chem. 2019 Jul 19;84(14):9358-9363. doi: 10.1021/acs.joc.9b01149. Epub 2019 Jun 17. PubMed PMID: 31244165. 11: Khoronenko VE, Malanova AS, Baskakov DS, Ryabov AB, Pikin OV. [Regional and peripheral blockades for prevention of chronic post-thoracotomy pain syndrome in oncosurgical practice]. Khirurgiia (Mosk). 2017;(8):58-63. doi: 10.17116/hirurgia2017858-63. Russian. PubMed PMID: 28805780. 12: Zhong XZ, Wang GC, Wang Y, Zhang XQ, Ye WC. [Monomeric indole alkaloids from the aerial parts of Catharanthus roseus]. Yao Xue Xue Bao. 2010 Apr;45(4):471-4. Chinese. PubMed PMID: 21355212. 13: Ishikawa H, Elliott GI, Velcicky J, Choi Y, Boger DL. Total synthesis of (-)- and ent-(+)-vindoline and related alkaloids. J Am Chem Soc. 2006 Aug 16;128(32):10596-612. PubMed PMID: 16895428; PubMed Central PMCID: PMC2531198. 14: Heureux N, Wouters J, Markó IE. Sequential acid/base-catalyzed polycyclization of tryptamine derivatives. A rapid access to Büchi's ketone. Org Lett. 2005 Nov 10;7(23):5245-8. PubMed PMID: 16268549.