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IKD-8344 Sale

目录号 : GC45959

A macrocyclic dilactone with diverse biological activities

IKD-8344 Chemical Structure

Cas No.:129046-69-1

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1mg
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产品描述

IKD-8344 is a macrocyclic dilactone originally isolated from an actinomycete species and has diverse biological activities, including anticancer, antimicrobial, and anthelmintic properties.1,2,3 It is cytotoxic to L5178Y murine leukemia cells (IC50 = 0.54 ng/ml).1 IKD-8344 inhibits growth of the mycelial form of C. albicans (MIC = 6.25 μg/ml) and potentiates the activity of polymyxin B against the multidrug-resistant pathogenic bacterium B. cenocepacia.2,3 It is active against T. spiralis in vitro and in vivo.1

|1. Minami, Y., Yoshida, K., Azuma, R., et al. Structure of a novel macrodiolide antibiotic IKD-8344. Tetrahedron Lett. 33(48), 7373-7376 (1992).|2. Hwang, E.I., Yun, B.S., Yeo, W.H., et al. Compound IKD-8344, a selective growth inhibitor against the mycelial form of Candida albicans, isolated from Streptomyces sp. A6792. J. Microbiol. Biotechnol. 15(4), 909-912 (2005).|3. Loutet, S.A., El-Halfawy, O.M., Jassem, A.N., et al. Identification of synergists that potentiate the action of polymyxin B against Burkholderia cenocepacia. Int. J. Antimicrob. Agents 46(4), 376-380 (2015).

Chemical Properties

Cas No. 129046-69-1 SDF
Canonical SMILES O=C1O[C@]([C@@H](C)[C@]2([H])CC[C@@H](C)O2)([H])C[C@@]3([H])O[C@@](CC3)([H])[C@@H](C)C(C[C@@]4([H])O[C@](CC4)([H])[C@H](C)C(O[C@]([C@@H](C)[C@]5([H])CC[C@@H](C)O5)([H])C[C@@](CC6)([H])O[C@@]6([H])[C@@H](C)C(C[C@@](CC7)([H])O[C@]7([H])[C@@H]1C)=O)=O)=O
分子式 C48H76O12 分子量 845.1
溶解度 DMSO: soluble,Ethanol: soluble,Methanol: soluble 储存条件 Store at -20°C
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1 mM 1.1833 mL 5.9165 mL 11.8329 mL
5 mM 0.2367 mL 1.1833 mL 2.3666 mL
10 mM 0.1183 mL 0.5916 mL 1.1833 mL
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Research Update

Three rings in one step: a quick approach to IKD-8344

Angew Chem Int Ed Engl 2012 May 14;51(20):4968-71.PMID:22492554DOI:10.1002/anie.201201395.

A highly efficient enantioselective total synthesis of the natural antibiotic IKD-8344 is achieved through a convergent route. This route features an otherwise impossible concurrent formation of the THF rings from a linear polyketide precursor through intramolecular O alkylations of mesylates in competition with normally rather facile β elimination and/or α racemization reactions (see scheme, Ms=methanesulfonyl).

Synthesis of enantiopure termini-differentiated heptane stereotriads. Application to side chain-functionalized tetrahydrofurans of IKD-8344

Org Lett 2000 Jul 27;2(15):2181-4.PMID:10930238DOI:10.1021/ol005791o.

Enantiopure epoxy cycloheptenyl sulfones syn-7b and anti-7b are prepared in five high-yielding and stereospecific operations from 1, 3-cycloheptadiene. These substrates serve as effective precursors for cis- and trans-substituted tetrahydrofurans (12, 10) which are segments of the antineoplastic agent IKD-8344.