Spirotryprostatin ACAS# 182234-25-9 |
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| Cas No. | 182234-25-9 | SDF | Download SDF |
| PubChem ID | 10408374 | Appearance | Powder |
| Formula | C22H25N3O4 | M.Wt | 395.5 |
| Type of Compound | Alkaloids | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Chemical Name | (3S,5S,6S,9S)-6'-methoxy-6-(2-methylprop-1-enyl)spiro[1,7-diazatricyclo[7.3.0.03,7]dodecane-5,3'-1H-indole]-2,2',8-trione | ||
| SMILES | CC(=CC1C2(CC3N1C(=O)C4CCCN4C3=O)C5=C(C=C(C=C5)OC)NC2=O)C | ||
| Standard InChIKey | MQJKGSIAJNXSCM-ORGXJRBJSA-N | ||
| Standard InChI | InChI=1S/C22H25N3O4/c1-12(2)9-18-22(14-7-6-13(29-3)10-15(14)23-21(22)28)11-17-19(26)24-8-4-5-16(24)20(27)25(17)18/h6-7,9-10,16-18H,4-5,8,11H2,1-3H3,(H,23,28)/t16-,17-,18-,22-/m0/s1 | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
Spirotryprostatin A Dilution Calculator
Spirotryprostatin A Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.5284 mL | 12.6422 mL | 25.2845 mL | 50.5689 mL | 63.2111 mL |
| 5 mM | 0.5057 mL | 2.5284 mL | 5.0569 mL | 10.1138 mL | 12.6422 mL |
| 10 mM | 0.2528 mL | 1.2642 mL | 2.5284 mL | 5.0569 mL | 6.3211 mL |
| 50 mM | 0.0506 mL | 0.2528 mL | 0.5057 mL | 1.0114 mL | 1.2642 mL |
| 100 mM | 0.0253 mL | 0.1264 mL | 0.2528 mL | 0.5057 mL | 0.6321 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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Total Synthesis of Spirotryprostatins through Organomediated Intramolecular Umpolung Cyclization.[Pubmed:30609181]
Chemistry. 2019 Feb 26;25(12):3005-3009.
Cyclodipeptide 2,5-diketopiperazines (DKP) are privileged structural units present in drugs and natural alkaloids. This work reports a new method for the synthesis of biologically important DKP scaffolds based on an intramolecular nucleophilic alpha-addition of general amides towards an alkynamide system. The utility of this umpolung cyclization mediated by trimethyl phosphine and l-glutamic acid is highlighted by its application to the concise total syntheses of 6-methoxyspirotryprostatin B (the first total synthesis), Spirotryprostatin A, and spirotryprostatin B.
Total synthesis and biological evaluation of spirotryprostatin A analogs.[Pubmed:28906026]
Chirality. 2017 Nov;29(11):737-746.
Based on the Spirotryprostatin A structure, a series of compounds belonging to spiro-indolyl diketopiperazine structural class were designed and synthesized, which embody an oxindole with an all-carbon quaternary stereocenter. The total synthesis can efficiently be accessed in a seven-step reaction sequence with 18-28% overall yield from commercially available materials, and a highly enantioselective 1,3-dipolar cycloaddition, N-acylation of the resulting stereochemically complex spiro[pyrrolidin-3,3'-oxindole]s core with Fmoc-L-pro-Cl and spontaneous ring closure upon N-deprotection were obtained. The synthesized compounds 13a-e and 15a-e were evaluated for their antibacterial activities. The result showed that compounds 13b and 15b were active only against Gram-positive bacteria, and selective antibacterial activity was exhibited by compounds 13d and 13e against Streptococcus lactis. Further, all the remaining compounds showed a certain degree of antibacterial activity. In addition, the structure-activity relationship is also discussed.
Fumigaclavine I, a new alkaloid isolated from endophyte Aspergillus terreus.[Pubmed:26721713]
Chin J Nat Med. 2015 Dec;13(12):937-41.
The present study was designed to isolate and purify chemical constituents from solid culture of endophyte Aspergillus terreus LQ, using silica gel column chromatography, gel filtration with Sephadex LH-20, and HPLC. Fumigaclavine I (1), a new alkaloid, was obtained, along with seven known compounds, including fumigaclavine C (2), rhizoctonic acid (3), monomethylsulochrin (4), chaetominine (5), Spirotryprostatin A (6), asperfumoid (7), and lumichrome (8). The structure of compound 1 was elucidated by various spectroscopic analyses (UV, MS, 1D and 2D NMR). The in vitro cytotoxicity of compound 1 was determined by MTT assay in human hepatocarcinoma cell line SMMC-7721, showing weaker cytotoxicity, compared with cisplatin, a clinically used cancer chemotherapeutic agent.
Distinct mechanisms for spiro-carbon formation reveal biosynthetic pathway crosstalk.[Pubmed:24121553]
Nat Chem Biol. 2013 Dec;9(12):818-25.
Spirotryprostatins, an indole alkaloid class of nonribosomal peptides isolated from Aspergillus fumigatus, are known for their antimitotic activity in tumor cells. Because spirotryprostatins and many other chemically complex spiro-carbon-bearing natural products exhibit useful biological activities, identifying and understanding the mechanism of spiro-carbon biosynthesis is of great interest. Here we report a detailed study of spiro-ring formation in spirotryprostatins from tryprostatins derived from the fumitremorgin biosynthetic pathway, using reactants and products prepared with engineered yeast and fungal strains. Unexpectedly, FqzB, an FAD-dependent monooxygenase from the unrelated fumiquinazoline biosynthetic pathway, catalyzed spiro-carbon formation in Spirotryprostatin A via an epoxidation route. Furthermore, FtmG, a cytochrome P450 from the fumitremorgin biosynthetic pathway, was determined to catalyze the spiro-ring formation in spirotryprostatin B. Our results highlight the versatile role of oxygenating enzymes in the biosynthesis of structurally complex natural products and indicate that cross-talk of different biosynthetic pathways allows product diversification in natural product biosynthesis.
Exploiting Sm(II) and Sm(III) in SmI2-initiated reaction cascades: application in a tag removal-cyclisation approach to spirooxindole scaffolds.[Pubmed:21617813]
Org Biomol Chem. 2011 Jul 21;9(14):5104-8.
A tag removal-cyclisation sequence is described that is initiated by reduction using a Sm(II) species and completed by a Sm(III) Lewis acid that is formed in an earlier stage. Therefore, the reaction cascade utilises both oxidation states of a samarium reagent in discrete steps and allows access to privileged, pyrrolidinyl-spirooxindole scaffolds and analogues inspired by the anti-cancer natural product Spirotryprostatin A.
Asymmetic organocatalytic 1,3-dipolar cycloaddition of azomethine ylide to methyl 2-(2-nitrophenyl)acrylate for the synthesis of diastereoisomers of spirotryprostatin A.[Pubmed:21486026]
Org Lett. 2011 May 6;13(9):2418-21.
The total synthesis of two diastereomers of Spirotryprostatin A has been established starting with an asymmetric 1,3-dipolar cycloaddition of methyl 2-(2-nitrophenyl)acrylate with azomethine ylides catalyzed by a Bronsted acid.
A concise synthesis of spirotryprostatin A.[Pubmed:15524455]
Org Lett. 2004 Nov 11;6(23):4249-51.
The preparation of two new synthons, 2,5- and 2,6-dibromotryptophan esters, and their use in diastereoselective intramolecular N-acyliminium ion spirocyclization methodology for the rapid construction of Spirotryprostatin A and analogues are described.
Concise, asymmetric total synthesis of spirotryprostatin A.[Pubmed:12917000]
Org Lett. 2003 Aug 21;5(17):3135-7.
[structure: see text] The structurally intriguing cell-cycle inhibitor Spirotryprostatin A has been synthesized utilizing an azomethine ylide dipolar cycloaddition reaction as the key step. This pentacyclic alkaloid contains a prenylated tryptophan-derived oxindole moiety that has been created in a regiocontrolled and stereocontrolled manner in a single step.
A biomimetic total synthesis of (-)-spirotryprostatin B and related studies.[Pubmed:10959875]
J Org Chem. 2000 Jul 28;65(15):4685-93.
The prenylated natural products Spirotryprostatin A and B derived from the Trp-Pro diketopiperazine also feature an oxidative rearrangement of the indole to form a spirooxindole. Synthetically, formation of the oxindole ring was stereoselectively accomplished by reaction of the appropriate indole precursor with N-bromosuccinimide. For optimum results, the oxidation should be carried out prior to diketopiperazine cyclization. In this manner, we have synthesized the tetrahydro- and dihydro- analogues of spirotryprostatin B in four steps from L-tryptophan methyl ester. The dihydro derivative was then converted to spirotryprostatin B by unsaturation of the pyrrolidine ring to a pyrroline, thus unambiguously confirming the structure of the natural product.
The Total Synthesis of Spirotryprostatin A.[Pubmed:29711010]
Angew Chem Int Ed Engl. 1998 May 4;37(8):1138-1140.
Eight concise steps suffice for the first total synthesis of the title compound 1, which inhibits the transitions from the G2 and M phases into the next phases of the cell cycle. Key steps in the synthesis are a stereocontrolled oxidative rearrangement of an indole to form the chiral spiroindolinone nucleus and a regioselecitve sulfoxide elimination.
