Synthetic approaches toward mitomycins: construction of p-quinone moiety on 1-benzazocine derivative

Yoshida, Kiyoshi; Nakajima, Souta; Ohnuma, Takeshi; Ban, Yoshio; Shibasaki, Masakatsu; Aoe, Keiichi; Date, Tadamasa

doi:10.1021/jo00257a031

Cited by 31 publications

(8 citation statements)

References 2 publications

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“…This scheme was successfully employed by the same group for the synthesis of a decarbamoyloxymitomycin derivative [ 175 – 176 ]. Compound 271 was obtained readily from commercially available 2-amino-5-nitrotoluene 269 in 94% overall yield.…”

Section: Discussionmentioning

confidence: 99%

Mitomycins syntheses: a recent update

Andrez¹

2009

Beilstein J. Org. Chem.

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SummaryMitomycins are a class of very potent antibacterial and anti-cancer compounds having a broad activity against a range of tumours. They have been used in clinics since the 1960’s, and the challenges represented by their total synthesis have challenged generations of chemists. Despite these chemical and medicinal features, these compounds, in racemic form, have succumbed to total synthesis only four times over the last 30 years.

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Section: Discussionmentioning

confidence: 99%

Mitomycins syntheses: a recent update

Andrez¹

2009

Beilstein J. Org. Chem.

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“…Most synthetic routes for quinoid cores involve hydroquinone oxidation with reagents such as Jones reagent; Fremy's salt (MacKenzie et al, 1986); LTA (Yoshida et al, 1988); DDQ (Pirrung et al, 2001); DMP (Nicolau et al, 2002); CAN (Heckrodt and Mulzer, 2003a, b); species with transition metal cores such as Ru (Murahashi et al, 1996), Ti, Mo, and Re (Adam et al, 1994); and ambient air (Kita et al, 2001). More sophisticated alternatives include Suzuki couplings between Fisher alkoxy carbenes and a boronic acid (Davies et al, 2001), thermal reactions between ciclobutane-1,2-diones and terminal alkynes (Liebeskind et al, 1992), and benzoin condensations (Hachisu et al, 2003).…”

Section: Synthetic Methodsmentioning

confidence: 99%

Quinoid systems in chemistry and pharmacology

et al. 2015

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In this paper, we present a brief review of quinoid systems, focusing on their chemical synthesis over the last decade. We address not only major methods of synthesizing quinoids, but also their involvement in biological processes. We highlight their medical relevance and versatility, including antitumor, antiretroviral, or antihypertensive agents, properties determined by their various patterns of substitution. Graphical AbstractKeywords Quinone Á Synthesis Á Cytotoxicity Á Natural products Á Pharmacology Á Redox Abbreviations 3a-HSD 3a-Hydroxysteroid dehydrogenase AIDS Acquired Immune Deficiency Syndrome AlnA Alnumycin A AlnB Alnumycin B BAQ Benzanthracene quinone (7,12-benzo[a] anthraquinone) BPQ Benzo[a]pyrene-7,8-dione CAN Ceric ammonium nitrate CC 50 50 % Cytotoxic concentration CDC25 Cell division cycle phosphatases Cyt Ferricytochrome d-A 2 0 -Deoxyadenosine DBU 1,8-Diazabicyclo[5.4.0]undec-7-ene DDQ 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone d-G, d-Guo 2'-Deoxyguanosine DMF N,N-dimethylformamide DMP Dess-Martin periodinane DMSO

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“…An improved 15-step synthesis of 15 as a right-ring model from the 3-hydroxy-4-methoxy-5-methylbenzandehyde derivative 21 18) was achieved, as shown in Chart 3B. 19) Condensation of 21 with 1,4-diacetylpiperazine-2,5-dione (22) in the presence of potassium tert-butoxide in DMF gave 3-arylidenepiperazine-2,5-dione (23) in 74% yield following the procedure of Gallina and Liberatori. 20,21) The secondary amine of 23 was protected with the 4-methoxybenzyl group to give 24, which was subjected to successive treatment with hydrazine hydrate followed by methylation to afford 25 in 74% overall yield.…”

Section: Biographymentioning

confidence: 99%

“…With the phenol model 15 in hand, we examined how it could conform to the proposed biosynthetic process, as shown in Chart 2. 22) Oxidation of 15 with bis(salicidene) ethylidene)ethylene-diiminocobalt(II) (salcomine) 23) in DMF at 25 °C for 5 h afforded the p-quinone 30 in 64% yield. It was identical in all respects to an authentic sample, which was obtained by 10N HNO 3 oxidation of 17 in 87% yield (Chart 4).…”

Section: Biographymentioning

confidence: 99%

“…Following our working hypothesis, we reported the model transformation from 30 to 54, as shown in Chart 9. 39) Reduction of the lactam 30 22) with 65% toluene solution of sodium bis-(2-methoxyethoxy) aluminium hydride (Red-Al) in THF at 0 °C for 1 h yielded the leuco compound 51. After the reaction mixture was quenched with AcOH, an aqueous solution of KCN was added dropwise over 10 min, and this mixture was stirred at 25 °C for 1 h to give a mixture of 52 and 53, which in turn was subjected to oxidation with 60% HNO 3 to give 53 in 74% overall yield from 30.…”

Section: Thiq Marine Natural Products From Thai Marine Organismsmentioning

confidence: 99%

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Chemical Research on Antitumor Isoquinoline Marine Natural Products and Related Compounds

Saito

2021

Chem. Pharm. Bull.

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The biologically active, naturally occurring 1,2,3,4-tetrahydroisoquinoline-quinone (THIQ) family members isolated from Actinomycetes and marine organisms have been studied thoroughly over the past five decades. Among them, marine natural products along with their reduced compounds, such as renieramycins and ecteinascidins, have attracted interest due to their fantastic structures and meager availability in nature as well as their potent antitumor profiles. As part of our search for new anticancer metabolites through the isolation and characterization of anticancer THIQ compounds from Thai marine animals, we have developed a fascinating THIQ natural product chemistry and medicinal chemistry based on knowledge of the chemistry of saframycin antibiotics as well as their isolation, characterization, transformation, partial synthesis, and total synthesis. This review mainly presents our contributions during 1999-2019 to the field of research on biologically active renieramycin along with ecteinascidin marine natural products.

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Synthetic approaches toward mitomycins: construction of p-quinone moiety on 1-benzazocine derivative

Cited by 31 publications

References 2 publications

Mitomycins syntheses: a recent update

Mitomycins syntheses: a recent update

Quinoid systems in chemistry and pharmacology

Chemical Research on Antitumor Isoquinoline Marine Natural Products and Related Compounds

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