About: Discovery, synthesis, and optimization of an N-alkoxy indolylacetamide against HIV-1 carrying NNRTI-resistant mutations from the Isatis indigotica root

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About: Discovery, synthesis, and optimization of an N-alkoxy indolylacetamide against HIV-1 carrying NNRTI-resistant mutations from the Isatis indigotica root Goto Sponge NotDistinct Permalink

An Entity of Type : schema:ScholarlyArticle, within Data Space : wasabi.inria.fr associated with source document(s)

Attributes	Values
type	Academic Article research paper schema:ScholarlyArticle
isDefinedBy	Covid-on-the-Web dataset
title	Discovery, synthesis, and optimization of an N-alkoxy indolylacetamide against HIV-1 carrying NNRTI-resistant mutations from the Isatis indigotica root
Creator	Ba, Mingyu Chen, Minghua Guo, Qinglan Guo, Ying Shi, Jiangong Xin, Yijing Xu, Chengbo Zhu, Chenggen
source	Elsevier; Medline; PMC
abstract	Abstract From an aqueous decoction of the traditional Chinese medicine “ban lan gen” (the Isatis indigotica root), an antiviral natural product CI - 39 was isolated as an NNRTI (non-nucleoside reverse transcriptase inhibitor) (EC50 = 3.40 μM). Its novel structure was determined as methyl (1-methoxy-1H-indol-3-yl)acetamidobenzoate by spectroscopic data and confirmed by single crystal X-ray diffraction. Through synthesis and structure-activity relationship (SAR) investigation of CI - 39 and 57 new derivatives (24 with EC50 values of 0.06–8.55 μM), two optimized derivatives 10f and 10i (EC50: 0.06 μM and 0.06 μM) having activity comparable to that of NVP (EC50 = 0.03 μM) were obtained. Further evaluation verified that 10f and 10i were RT DNA polymerase inhibitors and exhibited better activities and drug resistance folds compared to NVP against seven NNRTI-resistant strains carrying different mutations. Especially, 10i (EC50 = 0.43 μM) was more active to the L100I/K103N double-mutant strain as compared to both NVP (EC50 = 0.76 μM) and EFV (EC50 = 1.08 μM). The molecular docking demonstrated a possible binding pattern between 10i and RT and revealed activity mechanism of 10i against the NNRTI-resistant strains.
has issue date	2020-03-01(xsd:dateTime)
bibo:doi	10.1016/j.ejmech.2020.112071
bibo:pmid	32004936
has license	els-covid
sha1sum (hex)	96071f2ddd4192c50ff7bbe2c72b08f6d7210b2c
schema:url	https://doi.org/10.1016/j.ejmech.2020.112071
resource representing a document's title	Discovery, synthesis, and optimization of an N-alkoxy indolylacetamide against HIV-1 carrying NNRTI-resistant mutations from the Isatis indigotica root
has PubMed Central identifier	PMC7111291
has PubMed identifier	32004936
schema:publication	European Journal of Medicinal Chemistry
resource representing a document's body	covid:96071f2ddd4192c50ff7bbe2c72b08f6d7210b2c#body_text
is schema:about of	named entity 'HIV-1' named entity 'ban' named entity 'data' named entity 'mutations' named entity 'ROOT' named entity 'DETERMINED' named entity 'MUTATIONS' named entity 'FOLDS' named entity 'OBTAINED' named entity 'GEN' named entity 'DATA' named entity 'NEW' named entity '0.06' named entity 'STRUCTURE' named entity 'CONFIRMED BY' named entity 'DRUG RESISTANCE' named entity 'NVP' named entity 'LAN' named entity 'TRADITIONAL CHINESE MEDICINE' named entity 'NNRTI' named entity 'ISATIS INDIGOTICA' named entity 'DNA POLYMERASE INHIBITORS' named entity 'SYNTHESIS' named entity 'STRUCTURE-ACTIVITY RELATIONSHIP' named entity 'SEVEN' named entity '1H-INDOL-3-YL' named entity 'BETTER' named entity 'RESISTANT' named entity '10I' named entity 'RESISTANT' named entity 'ROOT' named entity 'SINGLE CRYSTAL X-RAY DIFFRACTION' named entity 'NOVEL' named entity 'ACTIVITY' named entity 'VALUES' named entity 'DIFFERENT' named entity 'DECOCTION' named entity 'NUCLEOSIDE REVERSE TRANSCRIPTASE INHIBITOR' named entity 'CARRYING' named entity 'ITS' named entity 'VERIFIED' named entity 'INVESTIGATION' named entity 'NNRTI' named entity 'ISATIS INDIGOTICA' named entity 'MUTATIONS' named entity 'ALKOXY' named entity 'SYNTHESIS' named entity 'OPTIMIZATION' named entity 'AQUEOUS' named entity 'COMPARED' named entity 'NATURAL PRODUCT' named entity 'STRAINS' named entity 'EVALUATION' named entity 'ISOLATED' named entity 'ACTIVITIES' named entity 'METHYL' named entity 'ANTIVIRAL' named entity '0.03' named entity 'METHOXY' named entity 'CARRYING' named entity 'DISCOVERY' covid:arg/96071f2ddd4192c50ff7bbe2c72b08f6d7210b2c named entity 'derivatives' named entity 'structure-activity relationship' named entity '3.5' named entity 'Haiyang' named entity 'silica gel' named entity 'MeOH' named entity 'indole' named entity 'DMSO' named entity '1.03' named entity '0.98' named entity 'Santa Clara, CA' named entity '13C NMR'

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