Regiospecific ring-opening reactions of β-aziridinyl α,β-enoates with acids: application to the stereoselective synthesis of a couple of diastereoisomeric (E )-alkene dipeptide isosteres from a single β-aziridinyl α,β-enoate and to the convenient preparation of amino alcohols bearing α,β-unsaturated ester groups

Tamamura, Hirokazu; Yamashita, M.; Nakajima, Yutaka; Sakano, Koichi; Otaka, Akira; Ohno, Hiroaki; Ibuka, Toshiro; Fujii, Nobutaka

doi:10.1039/a904671b

Cited by 38 publications

(19 citation statements)

References 37 publications

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“…However, when the same substrate was reacted with trifluoroacetic acid, β ‐hydroxy product 8 was obtained in 82 % yield. The trifluoroacetate group is highly labile, and hydrolysis takes place during flash column chromatography on silica gel as reported in the literature …”

Section: Resultsmentioning

confidence: 96%

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Synthesis of Functionalized Novel α‐Amino‐β‐alkoxyphosphonates through Regioselective Ring Opening of Aziridine‐2‐phosphonates

Polat-Çakır

Beksultanova

Doğan

2019

Helvetica Chimica Acta

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Aziridines are highly useful compounds as building blocks for the synthesis of important organic compounds. Amino acid synthesis by aziridine ring opening reaction is a good example to the use of aziridines. Although this reaction is studied by many groups, the synthesis of amino phosphonic acids is less explored. In this study, we have carried out the ring opening reaction of aziridinyl phosphonates with a variety of alcohols including the more functional propargylic and allylic alcohols. These reactions provided functionalized α‐amino‐β‐alkoxyphosphonates in 40–91 % yield.

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Section: Resultsmentioning

confidence: 96%

“…The trifluoroacetate group is highly labile, and hydrolysis takes place during flash column chromatography on silica gel as reported in the literature. [38]…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Functionalized Novel α‐Amino‐β‐alkoxyphosphonates through Regioselective Ring Opening of Aziridine‐2‐phosphonates

Polat-Çakır

Beksultanova

Doğan

2019

Helvetica Chimica Acta

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“…(Arg-L/D-Nal)-type EADIs, 5 and 8, were synthesized by the combination of stereoselective aziridinyl ring-opening reactions and organozinc-copper-mediated anti-S N 2' reactions toward a single substrate of γ,δ-cis-γ,δ-epimino (E)-α,β-enoate 1 (Fig. (3)) [92,93]. A (Nal-Gly)-type EADI 11 was also synthesized by the samarium diiodide (SmI 2 )-induced reduction of a γ-acetoxy-α,β-enoate 9 (Fig.…”

Section: -2 Low Molecular Weight Cxcr4 Antagonists Based On Cyclic mentioning

confidence: 99%

Development of Anti-HIV Agents Targeting Dynamic Supramolecular Mechanism: Entry and Fusion Inhibitors Based on CXCR4/CCR5 Antagonists and gp41-C34-Remodeling Peptides

Tamamura¹,

Otaka²,

Fujii

2005

CHR

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A molecular mechanism involved both in HIV-entry and -fusion steps has been disclosed in detail: The interaction of an HIV envelope protein, gp120, with chemokine receptors, CXCR4 and CCR5, which were identified as major co-receptors in association with CD4, triggers conformational changes in the gp120-gp41 (another envelope protein) complex, and subsequently forms the trimer-of-hairpins structure of gp41 followed by virus-cell membrane fusion. The elucidation of the above dynamic supramolecular mechanism in HIV-entry and -fusion has provided insights into new type of drugs that can block HIV infection. Based on this, we have developed not only coreceptor antagonists (1) but also fusion inhibitors (2). (1) Potent CXCR4 antagonists, T22 and T140, have been developed through the structure-activity relationship studies on tachyplesins and polyphemusins that are horseshoe crabs' antimicrobial peptides. T22, which was initially found to bind gp120 and CD4, and T140 selectively suppress T-cell line-tropic HIV-1 (X4-HIV-1) entry based on their specific binding to CXCR4. Furthermore, molecular-size reduction of T140 using cyclic pentapeptide templates brought us to find low molecular weight CXCR4 antagonists, such as FC131. (2) Artificial remodeling of a gp41 fragment, C34, has led to development of strong inhibitors of HIV-fusion into cells. These fusion inhibitors effectively block the formation of the trimer-of-hairpins structure of gp41. HIV-entry/fusion inhibitors such as CXCR4 antagonists and C34 analogs would improve the clinical chemotherapy of AIDS and HIV-infected patients. This review article focuses on our recent research on the development of the above two types of inhibitors, including comparative studies with several CXCR4 antagonists besides T22/T140-related compounds and other fusion inhibitors such as Fuzeon (T-20).

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“…Several FC131 analogues, in which such isosteres were substituted for the amide bond backbones, were developed on the basis of the synthetic strategy reported previously [64][65][66]. Structure-activity relationship studies of the isosteresubstituted compounds provided useful information concerning the reduction of peptide character [67].…”

Section: Discussionmentioning

confidence: 99%

Inhibitors of the Chemokine Receptor CXCR4: Chemotherapy of AIDS, Metastatic Cancer, Leukemia and Rheumatoid Arthritis

Tsutsumi¹,

Tamamura²,

Fujii

2007

LDDD

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The interaction between the chemokine, CXCL12 and its receptor, CXCR4 is known to be involved in several intractable disease processes, including HIV infection, cancer cell metastasis, leukemia cell progression and rheumatoid arthritis. It is conjectured that this interaction may be an important therapeutic target in all of these diseases, and various CXCR4 antagonists have been proposed as potential drugs. This article describes the development in our laboratory of a number of specific CXCR4 antagonists.

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Cited by 38 publications

References 37 publications

Synthesis of Functionalized Novel α‐Amino‐β‐alkoxyphosphonates through Regioselective Ring Opening of Aziridine‐2‐phosphonates

Synthesis of Functionalized Novel α‐Amino‐β‐alkoxyphosphonates through Regioselective Ring Opening of Aziridine‐2‐phosphonates

Development of Anti-HIV Agents Targeting Dynamic Supramolecular Mechanism: Entry and Fusion Inhibitors Based on CXCR4/CCR5 Antagonists and gp41-C34-Remodeling Peptides

Inhibitors of the Chemokine Receptor CXCR4: Chemotherapy of AIDS, Metastatic Cancer, Leukemia and Rheumatoid Arthritis

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