Anti-AIDS Agents. 46. Anti-HIV Activity of Harman, an Anti-HIV Principle from <i>Symplocos setchuensis</i>, and Its Derivatives

Ishida, Junko; Wang, Hui‐Kang; Oyama, Masayoshi; Cosentino, Mark; Hu, Chang‐Qi; Lee, Kuo‐Hsiung

doi:10.1021/np0101189

Cited by 110 publications

(43 citation statements)

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“…In 2000, Lee and co-workers were just first to report anti-HIV activity of a b-carboline alkaloid [15]. They prepared 28 derivatives of harmine and found that N-butylharmine was the most potent compound (EC 50 ¼ 0.037 mm) and possessed a good therapeutic index of 210 [16]. Yang and co-workers also found that some b-carboline derivatives inhibit HIV replication by interfering with the Tat-TAR interaction [17].…”

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confidence: 99%

“…Finally, substituted methyl b-carboline-3-carboxylates 5 were saponified by NaOH in MeOH to give the corresponding flazin analogues 6. Previous studies with harmine derivatives have shown that substitution of alkyl groups at N(9) of b-carboline ring system promotes the anti-HIV activity [16]. For this reason, two flazin analogues were designed and synthesized with a Me group or an Et group at N (9).…”

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Synthesis of Analogues of Flazin, in Particular, Flazinamide, as Promising Anti‐HIV Agents

Tang

Wang

et al. 2008

Chemistry & Biodiversity

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Flazin isolated from the fruiting bodies of Suillus granulatus was found to possess weak anti-HIV activity (EC(50)=2.36 microM, TI=12.1). To establish a SAR study, 46 flazin analogues were synthesized, and their anti-HIV activities were evaluated in vitro. Among them, flazinamide (9a) showed the most potent activity with an EC(50) value of 0.38 microM and a TI value of 312.0. The results suggested that appropriate substituents at positions 3, 1', and 5' of flazin might play a crucial role in determining their anti-HIV activities, and that flazinamide can be considered as a promising, readily available anti-HIV agent.

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confidence: 99%

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confidence: 99%

Synthesis of Analogues of Flazin, in Particular, Flazinamide, as Promising Anti‐HIV Agents

Tang

Wang

et al. 2008

Chemistry & Biodiversity

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“…It is therefore not surprising that analogs a, c, j, and r showed activity (IC 50 31.2, 29.2, 18.4, and 18.2 μM, respectively) against HIV-1 due to the presence of these moiety in the substituent. Alkylation of the indole nitrogen has been previously published to increase anti-HIV-1 activity [28].…”

Section: Anti-hiv-1mentioning

confidence: 99%

Chemical transformation and biological studies of marine sesquiterpene (S)-(+)-curcuphenol and its analogs

Gul

Hammond

Yousaf

et al. 2007

Biochimica et Biophysica Acta (BBA) - General Subjects

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Chemical transformation studies of the marine sesquiterpene phenol (S)-(+)-curcuphenol (1) isolated from the Jamaican sponges, Didiscus oxeata and Myrmekioderma styx, were accomplished. In order to optimize the activity and better understand the SAR of (S)-(+)-curcuphenol, nineteen semisynthetic analogs were prepared and evaluated for activity against infectious diseases. A number of analogs showed significant activity against Mtb and Leishmania donovani, while showing good to moderate activities in antibacterial and antifungal assays as well as against P. falciparium (D6 clone) and (W2 clone). The analogs a, c, h, and r exhibited Mtb activity with MICs of 24.6, 41.2, 6.90, and 50.5 μM, respectively. Analog f shows enhanced activity against L. donovani with an IC 50 of 0.6 μM and IC 90 of 40 μM respectively.

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“…Taxiresinol, isolated from T. wallichiana, showed noteworthy in vitro anticancer action against colon, ovarian, liver and breast cancer [26]. Matairesinol and pinoresinol were proved to have antileukemia activity and the ability to inhibit cAMP [27], as well as they were found to be an anti-HIV agents [28].…”

Section: Introductionmentioning

confidence: 99%

Identification and quantitative determination of pinoresinol in Taxus ×media Rehder needles, cell suspension and shoot cultures

et al. 2015

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The aim of our study was to investigate the presence and quantitative contents of lignans in the tissues of Taxus ×media. The presence of the lignans: pinoresinol, matairesinol and secoisolariciresinol was assessed in needles, shoots cultures and suspension culture. Pinoresinol was the only lignan found in the tissue of T. ×media. The total pinoresinol content in the needles and in the shoots was 1.24 mg/g dry weight (dw) and 0.69 mg/g dw, respectively. Most of the pinoresinol identified was appeared glycosidically bound. In needles, the amount of glycosidically bound pinoresinol (0.81 mg/g dw) was about twice as high as that of free pinoresinol (0.43 mg/g dw). The content of free and glycosidically bound pinoresinol showed the level of 0.18 mg/g dw and 0.51 mg/g dw, respectively in the in vitro shoot cultures. In the cell culture, no pinoresinol was found.

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Anti-AIDS Agents. 46. Anti-HIV Activity of Harman, an Anti-HIV Principle from Symplocos setchuensis, and Its Derivatives

Cited by 110 publications

References 10 publications

Synthesis of Analogues of Flazin, in Particular, Flazinamide, as Promising Anti‐HIV Agents

Synthesis of Analogues of Flazin, in Particular, Flazinamide, as Promising Anti‐HIV Agents

Chemical transformation and biological studies of marine sesquiterpene (S)-(+)-curcuphenol and its analogs

Identification and quantitative determination of pinoresinol in Taxus ×media Rehder needles, cell suspension and shoot cultures

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