45170-31-8Relevant articles and documents
Synthetic studies on quinoxaline antibiotics: II. Synthesis of triostin A
Shin,Otsuka
, p. 2203 - 2210 (1984)
Triostin A, a cyclic octadepsipeptide, was synthesized with Z-D-Ser[Boc-Ala-MeCys(Bzl)-MeVal]-OH and Z-n-Ser[H-Ala-MeCys(Bzl)-MeVal]-OTce as key intermediates. The synthetic antibiotic was compared with natural triostin A in terms of chromatographic behaviors, NMR spectra, and antomicrobial activity to establish their identity. The NMR data on S,S'-dibenzyldihydrotriostin A showed that this intermediate lacking the disulfide linkage also existed as two conformers in chloroform. This observation excludes the possibility that the conformer equilibrium known to occur with triostin A is a consequence of the reversed chirality of the disulfide bond. Triostin A, a cyclic octadepsipeptide, was synthesized with Z-D-Ser left bracket Boc-Ala-MeCys(Bzl)-MeVal right bracket -OH and Z- D-Ser left bracket H-Ala-MeCys(Bzl)-MeVal right bracket -OTce as key intermediates. The synthetic antibiotic was compared with natural triostin A in terms of chromatographic behaviors, NMR spectra, and antimicrobial activity to establish their identity. The NMR data on S,S prime -dibenzyldihydrotriostin A showed that this intermediate lacking the disulfide linkage also existed as two conformers in chloroform. This observation excludes the possibility that the conformer equilibrium known to occur with triostin A is a consequence of the reversed chirality of the disulfide bond.
First total synthesis of hoshinoamide A
Liu, Long,Rui, Zihan,Shao, Yutian,Xu, Shengtao,Yang, Yiming,Zhou, Haipin
supporting information, p. 2924 - 2931 (2022/01/12)
Hoshinoamides A, B and C, linear lipopeptides, were isolated from the marine cyanobacterium Caldora penicillata, with potent antiplasmodial activity against chloroquine-sensitive Plasmodium falciparum. Herein, we describe the first total synthesis of hosh
NOVEL CONNECTED BODY AND USE THEREOF IN SPECIFIC CONJUGATION BETWEEN BIOMOLECULE AND DRUG
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Paragraph 0260-0261, (2021/05/14)
PROBLEM TO BE SOLVED: To provide: a method for producing a connected body; a method for using the connected body in the production of a uniform conjugate; and a method for applying the conjugate in the treatment of cancer, infectious diseases, and autoimmune diseases. SOLUTION: A novel connected body is provided that includes a 2,3-di-substituted succinic acid group or a 2-mono-substituted or 2,3-di-substituted fumaric acid or maleic acid (trans (E)- or cis (Z)-butenedioic acid) group for conjugating 2 or more compounds/cytotoxic agents per connected body with a cell-binding molecule by specifically bridge-linking to a pair of thiol on the cell-binding molecule. The connected body is exemplified by the following general formula. SELECTED DRAWING: None COPYRIGHT: (C)2021,JPOandINPIT
Isolation and Total Synthesis of Kinenzoline, an Antitrypanosomal Linear Depsipeptide Isolated from a Marine Salileptolyngbya sp. Cyanobacterium
Kurisawa, Naoaki,Otomo, Keisuke,Iwasaki, Arihiro,Jeelani, Ghulam,Nozaki, Tomoyoshi,Suenaga, Kiyotake
, p. 12528 - 12536 (2021/09/20)
Kinenzoline (1), a new linear depsipeptide, was isolated from a marine Salileptolyngbya sp. cyanobacterium. Its structure was elucidated by spectroscopic analyses and degradation reactions. In addition, we achieved a total synthesis of 1 and confirmed its structure. Kinenzoline (1) showed highly selective antiproliferative activity against the causative organism of sleeping sickness, Trypanosoma brucei rhodesiense (IC50 4.5 μM), compared to normal human cells (WI-38, IC50 > 100 μM). Kinenzoline (1) is a promising lead compound for the development of new antitrypanosomal drugs.
CONJUGATION LINKERS CONTAINING 2,3-DIAMINOSUCCINYL GROUP
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Page/Page column 210, (2020/05/19)
Provided is a conjugate of a cytotoxic drug/molecule to a cell-binding molecule with a bis-linker (adual-linker) containing a 2, 3-diaminosuccinyl group. It also relates to preparation of the conjugate of a cytotoxic drug/molecule to a cell-binding molecule with the bis-linker, particularly when the drug having functional groups of amino, hydroxyl, diamino, amino-hydroxyl, dihydroxyl, carboxyl, hydrazine, aldehyde and thiol for conjugation with the bis-linker in a specific manner, as well as the therapeutic use of the conjugates.
Benzoazepine-Fused Isoindolines via Intramolecular (3 + 2)-Cycloadditions of Azomethine Ylides with Dinitroarenes
Wales, Steven M.,Rivinoja, Daniel J.,Gardiner, Michael G.,Bird, Melissa J.,Meyer, Adam G.,Ryan, John H.,Hyland, Christopher J. T.
supporting information, p. 4703 - 4708 (2019/06/27)
Aminobenzaldehydes bearing a pendant 3,5-dinitrophenyl group react thermally with N-substituted α-amino acids to form unprecedented benzoazepine-fused isoindolines. The reaction proceeds via a dearomatization/rearomatization sequence involving an intramolecular (3 + 2)-cycloaddition between the in situ formed azomethine ylide and the dinitroarene. Various glycine derivatives are tolerated as well as branched substrates based on cyclic, α-mono-, and α,α-disubstituted amino acids, giving single diastereomers in many cases. The method is scalable and gives products with a nitro group ready for further manipulation.
Synthesis of Majusculamides A and B
Nakajima, Daisuke,Sueyoshi, Kosuke,Orihara, Kensuke,Teruya, Toshiaki,Yokoshima, Satoshi
, p. 924 - 927 (2019/05/10)
The synthesis of two marine lipodipeptides, majusculamides A and B, is described. The key feature of this synthesis is the stereoselective construction of an α-methyl-β-keto-carboxamide moiety.
CONJUGATION OF A CYTOTOXIC DRUG WITH BIS-LINKAGE
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Paragraph 0717-0719, (2020/01/08)
What provided is the conjugation of cytotoxic to a cell-binding molecule with a bis-linker(dual-linker) as shown in Formula (I). It provides bis-linkage methods of making a conjugate of a cytotoxic drug molecule to a cell-binding agent in a specific manner. It also relates to application of the conjugates for the treatment of a cancer, or an autoimmune disease, or an infectious disease.
CONJUGATION LINKERS, CELL BINDING MOLECULE-DRUG CONJUGATES CONTAINING THE LIKERS, METHODS OF MAKING AND USES SUCH CONJUGATES WITH THE LINKERS
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Page/Page column 164, (2018/05/27)
The present invention relates to linkers having a group of propiolyl, substituted acryl (acryloyl), or disubstituted propanoyl, and using such linkers for the conjugation of compounds, in particular, cytotoxic agents to a cell-binding molecule.
Total synthesis and biological activity of dolastatin 16
Casalme, Loida O.,Yamauchi, Arisa,Sato, Akinori,Petitbois, Julie G.,Nogata, Yasuyuki,Yoshimura, Erina,Okino, Tatsufumi,Umezawa, Taiki,Matsuda, Fuyuhiko
supporting information, p. 1140 - 1150 (2017/02/10)
The total synthesis of dolastatin 16, a macrocyclic depsipeptide first isolated from the sea hare Dolabella auricularia as a potential antineoplastic metabolite by Pettit et al., was achieved in a convergent manner. Dolastatin 16 was reported by Tan to ex