Synonym
Lamellarin H; Lamellarine H;
IUPAC/Chemical Name
14-(3,4-dihydroxyphenyl)-2,3,11,12-tetrahydroxy-6a,14a-dihydro-6H-chromeno[4',3':4,5]pyrrolo[2,1-a]isoquinolin-6-one
InChi Key
KIRMMCLRVYLQSV-UHFFFAOYSA-N
InChi Code
InChI=1S/C25H17NO8/c27-14-2-1-11(6-15(14)28)21-22-13-8-18(31)19(32)9-20(13)34-25(33)24(22)26-4-3-10-5-16(29)17(30)7-12(10)23(21)26/h1-9,22,24,27-32H
SMILES Code
O=C1OC2=C(C(C13)C(C4=CC=C(O)C(O)=C4)=C5N3C=CC6=C5C=C(O)C(O)=C6)C=C(O)C(O)=C2
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
2934.99.03.00
Preparing Stock Solutions
The following data is based on the
product
molecular weight
459.41
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: Dialer C, Imbri D, Hansen SP, Opatz T. Synthesis of Lamellarin D Trimethyl Ether and Lamellarin H via 6π-Electrocyclization. J Org Chem. 2015 Nov 20;80(22):11605-10. doi: 10.1021/acs.joc.5b02194. Epub 2015 Oct 29. PubMed PMID: 26473557.
2: Manjappa KB, Syu JR, Yang DY. Visible-Light-Promoted and Yb(OTf)3-Catalyzed Constructions of Coumarin-Pyrrole-(Iso)quinoline-Fused Pentacycles: Synthesis of Lamellarin Core, Lamellarin D Trimethyl Ether, and Lamellarin H. Org Lett. 2016 Jan 15;18(2):332-5. doi: 10.1021/acs.orglett.5b03524. Epub 2016 Jan 7. PubMed PMID: 26741300.
3: You YC, Wang AL, Li DP, Yang G. Pyrrolo[2,1-alpha]isoquinoline as a skeleton for the synthesis of bioactive lamellarin H. Biomed Mater. 2006 Sep;1(3):L7-9. doi: 10.1088/1748-6041/1/3/L01. Epub 2006 Jun 23. PubMed PMID: 18458386.
4: Ridley CP, Reddy MV, Rocha G, Bushman FD, Faulkner DJ. Total synthesis and evaluation of lamellarin alpha 20-Sulfate analogues. Bioorg Med Chem. 2002 Oct;10(10):3285-90. PubMed PMID: 12150874.
5: Li Q, Jiang J, Fan A, Cui Y, Jia Y. Total synthesis of lamellarins D, H, and R and ningalin B. Org Lett. 2011 Jan 21;13(2):312-5. doi: 10.1021/ol1027877. Epub 2010 Dec 17. PubMed PMID: 21175172.
6: B Manjappa K, Lin JM, Yang DY. Construction of Pentacyclic Lamellarin Skeleton via Grob Reaction: Application to Total Synthesis of Lamellarins H and D. J Org Chem. 2017 Jul 21;82(14):7648-7656. doi: 10.1021/acs.joc.7b01061. Epub 2017 Jun 30. PubMed PMID: 28665125.
7: Ishibashi F, Tanabe S, Oda T, Iwao M. Synthesis and structure-activity relationship study of lamellarin derivatives. J Nat Prod. 2002 Apr;65(4):500-4. PubMed PMID: 11975488.
8: Lade DM, Pawar AB, Mainkar PS, Chandrasekhar S. Total Synthesis of Lamellarin D Trimethyl Ether, Lamellarin D, and Lamellarin H. J Org Chem. 2017 May 5;82(9):4998-5004. doi: 10.1021/acs.joc.7b00636. Epub 2017 Apr 24. PubMed PMID: 28421766.
