Stereoselective synthesis of squalamine dessulfate

Moriarty, Robert M.; Enache, Livia A.; Kinney, William A.; Allen, Colin; Canary, James W.; Tuladhar, Sudersan M.; Guo, Linghong

doi:10.1016/0040-4039(95)01011-6

Cited by 34 publications

(26 citation statements)

References 12 publications

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“…The lack of a large diaxial coupling with adjacent protons on C-11 indicates that the hydroxyl group is attached axially [J 11e,12 ) J 11a,12 ≈ 4 Hz (COSY)]. Characteristic of all aminosterols reported here is the broad singlet for H-7 found at δ 3.8 correlating with a carbon methine signal at δ 68 in methanol-d 4 .…”

Section: Resultsmentioning

confidence: 77%

“…The process includes (a) an extraction into water/acetic acid/ethanol/ammonium sulfate; (b) batch adsorption and extraction from XAD resin; (c) adsorption and elution from a cation exchange column (propylsulfonic acid resin); and, finally, (d) reversed-phase separation by HPLC (YMC-ODS column). Although squalamine is the most abundant aminosterol found in dogfish shark liver (400-800 mg, 0.001-0.002%), seven additional aminosterols (1)(2)(3)(4)(5)(6)(7) are found in amounts of 20-100 mg (0.00005-0.00025%) for a typical shark liver preparation (40 kg). Other minor aminosterols, found in trace quantities of <2 mg/40 kg shark liver, have not been fully characterized.…”

Section: Resultsmentioning

confidence: 99%

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Aminosterols from the Dogfish Shark Squalus acanthias

Mn¹,

Ae²,

La³

et al. 2000

J. Nat. Prod.

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119

106

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Seven new aminosterols related to squalamine (8) were isolated from the liver of the dogfish shark Squalus acanthias. Their structures (1-7) were determined using spectroscopic methods, including 2D NMR and HRFABMS. These aminosterols possess a relatively invariant cholestane skeleton with a trans AB ring junction, a spermidine or spermine attached equatorially at C3, and a steroidal side-chain that may be sulfated. The structure of the lone spermine conjugate, 7 (MSI-1436), was confirmed by its synthesis from (5alpha,7alpha, 24R)-7-hydroxy-3-ketocholestan-24-yl sulfate. Some members of this family of aminosterols exhibit a broad spectrum of antimicrobial activity comparable to squalamine.

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Section: Resultsmentioning

confidence: 77%

Section: Resultsmentioning

confidence: 99%

Aminosterols from the Dogfish Shark Squalus acanthias

Mn¹,

Ae²,

La³

et al. 2000

J. Nat. Prod.

Self Cite

119

106

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“…It is this structural moiety that is a part of the phloedictine A ( XXX ) and B ( XXXI ) molecules [22]. Stellettamides A ( XXXII ) and C ( XXXIII ), including a substituted octahydroindolizinium, may be regarded as products of a complex transformation of spermidine proceeding through a cyclization and deamination.…”

Section: The Structure Of Polyamines From Marine Organisms and Animalsmentioning

confidence: 99%

“…Phloedictines A (XXX) and B (XXXI) exhibit a high antibacterial activity in vitro and a moderate cytotoxicity (KB cells of the human nasopharyngic carcinoma) [22].…”

Section: Biological Activity Of Polyamines From Marine Organisms and mentioning

confidence: 99%

Polymethyleneamine Alkaloids of Animal Origin: I. Metabolites of Marine and Microbial Organisms

Salakhutdinov

2005

Russ J Bioorg Chem

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This review, issued in two parts, describes the information on the structure and biological activity of animal alkaloids derived from polymethyleneamines and produced by marine organisms, wasps, spiders, and microorganisms. Animal alkaloids are outstanding models for developing methods and drugs for the treatment of many human diseases. In the first part, we consider compounds produced by marine and microbial organisms. Some promising synthetic analogues of these alkaloids are used in developing modern preparations for the chelate therapy of excessive blood iron content and antituberculosis, antiproliferative, and immunosuppressive drugs.

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“…[12] The key step, establishing the C-24 stereochemistry, is the attachment of the side chain at C-22, using either (2R)-or (2S)-1,2-epoxy-3-methylbutane (55 or 56), to afford the corresponding squalamine dessulfate stereoisomer (Scheme 11).…”

Section: Synthesis Of Spermine and Spermidine Analogs Of Squalamine Amentioning

confidence: 99%

Recent Advances in the Synthesis of Spermine and Spermidine Analogs of the Shark Aminosterol Squalamine

Brunel¹,

Letourneux²

2003

Eur J Org Chem

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Great attention has recently been focused on the shark aminosterol squalamine (1) because of its important antimicrobial and antiangiogenic activities. Herein, we present the different series of spermine and spermidine analogs that have been synthesized. Many of the squalamine mimics demonstrate a broad spectrum activity against microorganisms. Squalamine is currently undergoing Phase II clinical trials in cancer patients. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

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Stereoselective synthesis of squalamine dessulfate

Cited by 34 publications

References 12 publications

Aminosterols from the Dogfish Shark Squalus acanthias

Aminosterols from the Dogfish Shark Squalus acanthias

Polymethyleneamine Alkaloids of Animal Origin: I. Metabolites of Marine and Microbial Organisms

Recent Advances in the Synthesis of Spermine and Spermidine Analogs of the Shark Aminosterol Squalamine

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