دورية أكاديمية
أعرض في EDS

Total Synthesis and Antimalarial Activity of 2-( p -Hydroxybenzyl)-prodigiosins, Isoheptylprodigiosin, and Geometric Isomers of Tambjamine MYP1 Isolated from Marine Bacteria.

التفاصيل البيبلوغرافية
العنوان: Total Synthesis and Antimalarial Activity of 2-( p -Hydroxybenzyl)-prodigiosins, Isoheptylprodigiosin, and Geometric Isomers of Tambjamine MYP1 Isolated from Marine Bacteria.
المؤلفون: Kancharla P; Department of Chemistry, Portland State University, Portland, Oregon 97201, United States., Li Y; Department of Veterans Affairs Medical Center, Portland, Oregon 97239, United States., Yeluguri M; Department of Chemistry, Portland State University, Portland, Oregon 97201, United States., Dodean RA; Department of Veterans Affairs Medical Center, Portland, Oregon 97239, United States., Reynolds KA; Department of Chemistry, Portland State University, Portland, Oregon 97201, United States., Kelly JX; Department of Chemistry, Portland State University, Portland, Oregon 97201, United States.; Department of Veterans Affairs Medical Center, Portland, Oregon 97239, United States.
المصدر: Journal of medicinal chemistry [J Med Chem] 2021 Jun 24; Vol. 64 (12), pp. 8739-8754. Date of Electronic Publication: 2021 Jun 10.
نوع المنشور: Journal Article; Research Support, N.I.H., Extramural; Research Support, Non-U.S. Gov't
اللغة: English
بيانات الدورية: Publisher: American Chemical Society Country of Publication: United States NLM ID: 9716531 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1520-4804 (Electronic) Linking ISSN: 00222623 NLM ISO Abbreviation: J Med Chem Subsets: MEDLINE
أسماء مطبوعة: Publication: Washington Dc : American Chemical Society
Original Publication: [Easton, Pa.] : American Chemical Society, [c1963-
مواضيع طبية MeSH: Antimalarials/*therapeutic use , Prodigiosin/*analogs & derivatives , Prodigiosin/*therapeutic use , Pyrroles/*therapeutic use, Animals ; Antimalarials/chemical synthesis ; Antimalarials/toxicity ; Female ; Hep G2 Cells ; Humans ; Mice ; Molecular Structure ; Parasitic Sensitivity Tests ; Plasmodium falciparum/drug effects ; Plasmodium yoelii/drug effects ; Prodigiosin/toxicity ; Pyrroles/chemical synthesis ; Pyrroles/toxicity ; Stereoisomerism ; Structure-Activity Relationship
مستخلص: Highly efficient and straightforward synthetic routes toward the first total synthesis of 2-( p -hydroxybenzyl)-prodigiosins ( 2 - 5 ), isoheptylprodigiosin ( 6 ), and geometric isomers of tambjamine MYP1 (( E / Z )- 7 ) have been developed. The crucial steps involved in these synthetic routes are the construction of methoxy-bipyrrole-carboxaldehydes (MBCs) and a 20-membered macrocyclic core and a regioselective demethylation of MBC analogues. These new synthetic routes enabled us to generate several natural prodiginines 24 - 27 in larger quantity. All of the synthesized natural products exhibited potent asexual blood-stage antiplasmodial activity at low nanomolar concentrations against a panel of Plasmodium falciparum parasites, with a great therapeutic index. Notably, prodiginines 6 and 24 - 27 provided curative in vivo efficacy against erythrocytic Plasmodium yoelii at 25 mg/kg × 4 days via oral route in a murine model. No overt clinical toxicity or behavioral change was observed in any mice treated with prodiginines and tambjamines.
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معلومات مُعتمدة: R01 AI141972 United States AI NIAID NIH HHS
المشرفين على المادة: 0 (Antimalarials)
0 (Pyrroles)
0 (tambjamine MYP1)
OL369FU7CJ (Prodigiosin)
تواريخ الأحداث: Date Created: 20210610 Date Completed: 20210825 Latest Revision: 20211214
رمز التحديث: 20240829
مُعرف محوري في PubMed: PMC8244818
DOI: 10.1021/acs.jmedchem.1c00748
PMID: 34111350
قاعدة البيانات: MEDLINE
الوصف
تدمد:1520-4804
DOI:10.1021/acs.jmedchem.1c00748