Diastereoselective Synthesis of Cyclopentanoids with Hydantoin and Isoxazoline Substituents

Kim, Huy Kang; Olmstead, Marilyn M.; Kurth, Mark J.

doi:10.1021/jo9714831

Cited by 29 publications

(19 citation statements)

References 17 publications

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“…The anticonvulsant properties of Phenytoin (Dilantin, Epilan), one of the important drugs employed for the treatment of generalized convulsions, are responsible for the synthesis of many hydantoin analogs [1][2][3]. The structural characteristics of hydantoins and spirohydantoins are interesting in view of the development of novel drugs [4] and for better understanding the structure-activity relationship.…”

Section: Introductionmentioning

confidence: 99%

Structure, conformation and hydrogen bonding of two amino-cycloalkanespiro-5-hydantoins

Todorov

Petrova²,

Naydenova

et al. 2009

Open Chemistry

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The crystal structures of 3-amino-cycloheptanespiro-4′-imidazolidine-2′,5′-dione (I) {systematic name: 3-amino-1,3-diazaspiro[4.6] undecane-2,4-dione} and 3-amino-cyclooctanespiro-4′-imidazolidine-2′,5′-dione (II) {systematic name: 3-amino-1,3-diazaspiro[4.7] dodecane-2,4-dione}, have been determined. In both compounds the polar hydantoin groups cause molecules to aggregate via N-H...O and N-H...N interactions, forming a layer structure, in which the cycloalkane rings project outwards from the central, more polar, region. The observed molecular structure is compared with that calculated by density functional theory methods.

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Section: Introductionmentioning

confidence: 99%

Structure, conformation and hydrogen bonding of two amino-cycloalkanespiro-5-hydantoins

Todorov

Petrova²,

Naydenova

et al. 2009

Open Chemistry

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“…The resultant acid and a variety of amines, including methylamine, benzylamine, and phenylethylamine, yielded amides 7a–7c under classic peptide coupling condition (HOBt, EDCI, DIPEA). Removal of the Boc group in compounds 7a–7c , followed by coupling with a series of 2‐ureidoacetic acid (prepared from L ‐valine or L ‐leucine with isocyanates; Park et al., 1998) afforded 8a–8q in moderate yields.…”

Section: Resultsmentioning

confidence: 99%

Design, synthesis, and antitumor activity evaluation of pretubulysin analogs

Fan

et al. 2021

Chem Biol Drug Des

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Pretubulysin, a biosynthetic precursor of the tubulysins, shows potent biological activity in a variety of tumor cell lines. Although there are several total synthesis routes to tubulysin and pretubulysin reported, the commercialization still has been hampered due to the complexity of the structure. To find structurally simpler pretubulysin analogs, a series of 2‐(3‐(methylamino)propyl)thiazole‐4‐carboxamides are designed and synthesized, and their anticancer activities are screened using MCF‐7 (breast cancer), and NCI‐H157 (lung cancer) cell lines. Taxol (IC50 = 0.01 µM) and pretubulysin are used as the control. Compounds 8c (IC50 = 0.05 µM, MCF‐7; 0.09 µM, NCI‐H157) and 8h (IC50 = 0.01 µM, MCF‐7; 0.02 µM, NCI‐H157) exhibited certain antitumor activities comparable to those of Taxol. The urea analogs of pretubulysin might represent a promising scaffold for the further development of novel antitumor drugs.

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“…Isolated radiochemical yields Chemistry. 2-Phenyloxazol-5(4H)-one (1), 23 ethyl (E)-2-((4bromobenzylidene)amino)acetate (13), 24 ethyl (Z)-1-((4bromobenzylidene)amino)cyclopent-3-ene-1-carboxylate ( 14), 24 and ethyl 1-aminocyclopent-3-ene-1-carboxylate (15) 24 were prepared according to previously reported procedures.…”

Section: ■ Conclusionmentioning

confidence: 99%

Synthesis, Radiolabeling, and Biological Evaluation of the cis Stereoisomers of 1-Amino-3-Fluoro-4-(fluoro-¹⁸F)Cyclopentane-1-Carboxylic Acid as PET Imaging Agents

Pickel

Voll

et al. 2020

J. Med. Chem.

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The non-natural cyclic amino acids (1S,3R,4S)-1-amino-3-fluoro-4-(fluoro-18 F)cyclopentane-1-carboxylic acid ([18F]9) and (1S,3S,4R)-1-amino-3-fluoro-4-(fluoro-18 F)cyclopentane-1-carboxylic acid ([18F]28) have been prepared in 10 and 1.7% decay corrected radiochemical yield, respectively, and in greater than 99% radiochemical purity. Cell assays in rat 9L gliosarcoma, human U87 ΔEGFR glioblastoma, and human DU145 androgen-independent prostate carcinoma tumor cells indicated that both compounds are substrates for amino acid transport primarily by system L, with some transport taking place via system ASC. In rats with 9L gliosarcoma, [18F]9 and [18F]28 provided high tumor to normal brain tissue ratios, with maximal ratios of 3.5 and 4.1, respectively. Biodistribution studies in healthy rats confirmed that both compounds are BBB permeable and that bladder accumulation is low until at least 5 min post injection.

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Diastereoselective Synthesis of Cyclopentanoids with Hydantoin and Isoxazoline Substituents

Cited by 29 publications

References 17 publications

Structure, conformation and hydrogen bonding of two amino-cycloalkanespiro-5-hydantoins

Structure, conformation and hydrogen bonding of two amino-cycloalkanespiro-5-hydantoins

Design, synthesis, and antitumor activity evaluation of pretubulysin analogs

Synthesis, Radiolabeling, and Biological Evaluation of the cis Stereoisomers of 1-Amino-3-Fluoro-4-(fluoro-¹⁸F)Cyclopentane-1-Carboxylic Acid as PET Imaging Agents

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Diastereoselective Synthesis of Cyclopentanoids with Hydantoin and Isoxazoline Substituents

Cited by 29 publications

References 17 publications

Structure, conformation and hydrogen bonding of two amino-cycloalkanespiro-5-hydantoins

Structure, conformation and hydrogen bonding of two amino-cycloalkanespiro-5-hydantoins

Design, synthesis, and antitumor activity evaluation of pretubulysin analogs

Synthesis, Radiolabeling, and Biological Evaluation of the cis Stereoisomers of 1-Amino-3-Fluoro-4-(fluoro-18F)Cyclopentane-1-Carboxylic Acid as PET Imaging Agents

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Synthesis, Radiolabeling, and Biological Evaluation of the cis Stereoisomers of 1-Amino-3-Fluoro-4-(fluoro-¹⁸F)Cyclopentane-1-Carboxylic Acid as PET Imaging Agents