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Bogonda, Ganganna,Kim, Hun Young,Oh, Kyungsoo American Chemical Society 2018 ORGANIC LETTERS Vol.20 No.9
<P>A direct acyl radical addition to 2<I>H</I>-indazoles has been achieved for the first time, where the less-aromatic <I>quinonoid</I> 2<I>H</I>-indazoles readily accepted radical species to the C-3 position. Motivated by the lack of direct acylation strategy for 2<I>H</I>-indazoles, the current method utilizes the radical acceptability of 2<I>H</I>-indazoles, discovering an ambient temperature reaction to provide facile access to a diverse array of 3-acyl-2<I>H</I>-indazoles with three points of structural diversification in 25%-83% yields.</P> [FIG OMISSION]</BR>
Synthesis and Structure Revision of Dimeric Tadalafil Analogue Adulterants in Dietary Supplements
Mandava, S.,Ganganna, B.,Hwang, Ju.,Jang, Y.,Hwang, Ji.,Samala, M.,Kim, K.-B.,Park, H.,Lee, J. H.,Baek, S. Y. Pharmaceutical Society of Japan 2017 Chemical & pharmaceutical bulletin Vol. No.
<P>A number of phosphodiesterase 5 (PDE5) inhibitors approved by authorities have been used successfully in the treatment of erectile dysfunction. These medicines must be prescribed carefully due to their adverse effects, but they and their analogues are being illegally added to dietary supplements. These illegal dietary supplements pose a significant risk to public health. Several dimeric tadalafil analogues have been synthesized for use as reference standards in the inspection of functional foods that are mainly advertised as sexual enhancement products. During the course of this synthesis, 1-Ibis(dimethylamino)methylenek1H-1,2,3triazolo14,5-blpyridinium 3-oxid hexafluorophosphate (HATU) was proven to be the reagent of choice for amide coupling to produce these dimeric tadalafil analogues. Moreover, the trans-isomer structures tentatively assigned for the isolated dimeric tadalafil analogues (bisprehomotadalafil and bisprecyclopentyltadalafil) found in dietary supplements are now revised to cis-isomer structures.</P>
Lee, Ji Hyun,Park, Han Na,Ganganna, Bogonda,Jeong, Ji Hye,Park, Sung-Kwan,Lee, Jongkook,Baek, Sun Young Informa UK (TaylorFrancis) 2016 Food additives & contaminants. Part A. Chemistry, Vol.33 No.6
<P>A newtadalafil analoguewas found, alongwith nortadalafil, using HPLC-DAD during the inspection of a health product sold without official approval. The analogue was separated using a semi-preparative HPLC system and its structure was determined by a combination of mass spectrometry and NMR spectroscopy. The compound was identified as a tadalafil analogue in which the N-methyl group of tadalafil was replaced with a tadalafil precursor moiety. Nuclear Overhauser effect spectroscopy experiments suggested a cis-relationship between the substituents on a piperidine ring in the tadalafilmoiety.</P>
Lee, Ji Hyun,Park, Han Na,Kim, Nam Sook,Park, Seongsoo,Bogonda, Ganganna,Oh, Kyungsoo,Kang, Hoil Elsevier Sequoia 2019 Forensic science international Vol.303 No.-
<P><B>Abstract</B></P> <P>With the increasing prevalence of obesity, the use of counterfeit drugs for weight loss is widespread owing to their easy and rapid availability. Since counterfeit weight-loss drugs are not prepared under the rigorous standard of Good Manufacturing Practice (GMP), they pose a risk to public health and cause significant side effects. To counteract the risk posed by counterfeit drugs, we investigated counterfeit weight-loss drugs seized by the Incheon Customs Services using UHPLC-PDA. Five of 23 confiscated samples with distinctive pink-coloured coating contained levothyroxine, sennoside A and B, and phenolphthalein in amounts ranging from 0.03–132.40 mg/g. In addition, three unknown compounds in one of the adulterated samples containing phenolphthalein were structurally elucidated by several analytical techniques. Their accurate masses corresponded to molecular formula of C<SUB>34</SUB>H<SUB>22</SUB>O<SUB>7</SUB>, C<SUB>34</SUB>H<SUB>20</SUB>O<SUB>6</SUB>, and C<SUB>20</SUB>H<SUB>12</SUB>O<SUB>3</SUB>, respectively. These compounds were identified as impurities, possibly produced during the synthesis of phenolphthalein or by improper removal during purification. These impurities were detected for the first time in counterfeit drugs.</P> <P><B>Highlights</B></P> <P> <UL> <LI> The 23 counterfeit weight-loss drugs were screened by UHPLC-PDA analysis. </LI> <LI> Five of samples were detected in range of 0.03–132.40 mg/g. </LI> <LI> Three unknown compounds in one sample were structurally elucidated by LC-HR–MS and NMR. </LI> <LI> They were first detected in counterfeit drugs and identified as phenolphthalein impurities. </LI> <LI> These impurities were possibly produced during the synthesis of phenolphthalein. </LI> </UL> </P>
Scalable synthesis of the C14–C23 fragment of Eribulin and Halichondrin B
Kim U Bin,Samala Srinivas,Kim Namhyeon,Bogonda Ganganna,Lago‐Santomé Hugo,Jeong Youngdo,Kim Jin,Jung Jaehun,Jeon Sung‐Hyun,Lee Seung Jong,신현석 대한화학회 2022 Bulletin of the Korean Chemical Society Vol.43 No.12
A novel, scalable approach to the C14–C23 fragment of eribulin mesylate is disclosed. Key 2,3-Wittig rearrangement is strategically effected via [Rh] mediated decomposition of 1,2,3-triazole intermediate to derive the 2,5-trans-tetrahydrofuran motif, enabling multi-kilogram access to the desired C14–C23 fragment.
Samala, Mallesham,Lu, Thien Nhan,Mandava, Suresh,Hwang, Jungjoong,Bogonda, Ganganna,Kim, Donghoon,Park, Haeil,Kim, Deukjoon,Lee, Jongkook American Chemical Society 2018 ORGANIC LETTERS Vol.20 No.20
<P>A stereoselective protection-free asymmetric total synthesis of (+)-chamuvarinin (<B>1</B>), a potent anticancer and antitrypanosomal agent, has been accomplished. The adjacently linked [bis(tetrahydrofuran)]tetrahydropyran (THF-THF-THP) core of this natural product with seven stereogenic centers was constructed in a completely substrate-controlled fashion. The inter-ring stereochemistry (<I>threo,threo,threo</I>) of the oxatricyclic core was established in a stereoselective fashion by a chelation-controlled Keck allylation, whereas the intraring <I>cis</I> or <I>trans</I> relative stereochemistry was controlled by a stereoselective internal alkylation.</P> [FIG OMISSION]</BR>