Esterification of Tertiary Amides by Alcohols Through C−N Bond Cleavage over CeO 2

ChemCatChem ◽  
2018 ◽  
Vol 11 (1) ◽  
pp. 449-456 ◽  
Author(s):  
Takashi Toyao ◽  
Md. Nurnobi Rashed ◽  
Yoshitsugu Morita ◽  
Takashi Kamachi ◽  
S. M. A. Hakim Siddiki ◽  
...  
Keyword(s):  
Bond Cleavage ◽  
Tertiary Amides

scholarly journals Front Cover: Esterification of Tertiary Amides by Alcohols Through C−N Bond Cleavage over CeO 2 (ChemCatChem 1/2019)

ChemCatChem ◽  
2019 ◽  
Vol 11 (1) ◽  
pp. 1-1 ◽  
Author(s):  
Takashi Toyao ◽  
Md. Nurnobi Rashed ◽  
Yoshitsugu Morita ◽  
Takashi Kamachi ◽  
S. M. A. Hakim Siddiki ◽  
...  
Keyword(s):  
Bond Cleavage ◽  
Front Cover ◽  
Tertiary Amides

ChemInform Abstract: Copper-Catalyzed Aerobic Oxidative Inert C-C and C-N Bond Cleavage: A New Strategy for the Synthesis of Tertiary Amides.

ChemInform ◽  
2015 ◽  
Vol 46 (11) ◽  
pp. no-no
Author(s):  
Xiuling Chen ◽  
Tieqiao Chen ◽  
Qiang Li ◽  
Yongbo Zhou ◽  
Li-Biao Han ◽  
...  
Keyword(s):  
Bond Cleavage ◽  
New Strategy ◽  
Tertiary Amides

Cisplatin-Triggered Bioorthogonal Decaging of Amide Bonds for Targeted-Drug Activation in vivo

2018 ◽  
Author(s):  
Benjamin Stenton ◽  
Bruno Oliveira ◽  
João Conde ◽  
Magda Negrão ◽  
Miguel Godinho Ferreira ◽  
...  
Keyword(s):  
Bond Cleavage ◽  
Xenograft Model ◽  
Amide Bonds ◽  
Control Drug ◽  
Tertiary Amide ◽  
Platinum Salts ◽  
First Choice ◽  
Tertiary Amides ◽  
Drug Activation

<p>Creating ways to control drug activation at specific tissues while sparing healthy tissues remains a major challenge. The administration of exogenous triggers offers the possibility for precise and traceless drug activation. However, ensuring localization of the trigger as well as the prodrug at the diseased tissue is complex while essential for therapeutic efficacy and to avoid side-toxicity. Cisplatin remains a first line option to treat 20% of all cancer patients and while clearing after 30 min from blood it concentrates in tumor tissues. Here, we demonstrate the use of the platinum-mediated bond cleavage of protected tertiary amides, which can occur in a catalytic manner under bioorthogonal conditions. Protected analogues of cytotoxic drugs 5-fluorouracil (5-FU) and monomethyl auristatin E (MMAE) were successfully activated using non-toxic amounts of platinum salts in cells. An otherwise fully stable and non-internalizing ADC built using a bifunctional linker featuring a tertiary amide protected MMAE was also bioorthogonally decaged in the presence of platinum salts for extracellular drug release. Finally, cisplatin-mediated activation of a prodrug 5-FU was shown in a colorectal zebrafish xenograft model leading to a significant tumor reduction. Considering cisplatin’s continued use as a first-choice treatment for many solid cancers and especially in colorectal cancer, we anticipate that our platinum-mediated decaging strategy will enhance cancer therapy by allowing tumor specific prodrug activation.</p>

Copper-Catalyzed Aerobic Oxidative Inert CC and CN Bond Cleavage: A New Strategy for the Synthesis of Tertiary Amides

2014 ◽  
Vol 20 (38) ◽  
pp. 12234-12238 ◽  
Author(s):  
Xiuling Chen ◽  
Tieqiao Chen ◽  
Qiang Li ◽  
Yongbo Zhou ◽  
Li-Biao Han ◽  
...  
Keyword(s):  
Bond Cleavage ◽  
New Strategy ◽  
Tertiary Amides

Cisplatin-Triggered Bioorthogonal Decaging of Amide Bonds for Targeted-Drug Activation in vivo

2018 ◽  
Author(s):  
Benjamin Stenton ◽  
Bruno Oliveira ◽  
João Conde ◽  
Magda Negrão ◽  
Miguel Godinho Ferreira ◽  
...  
Keyword(s):  
Bond Cleavage ◽  
Xenograft Model ◽  
Amide Bonds ◽  
Control Drug ◽  
Tertiary Amide ◽  
Platinum Salts ◽  
First Choice ◽  
Tertiary Amides ◽  
Drug Activation

<p>Creating ways to control drug activation at specific tissues while sparing healthy tissues remains a major challenge. The administration of exogenous triggers offers the possibility for precise and traceless drug activation. However, ensuring localization of the trigger as well as the prodrug at the diseased tissue is complex while essential for therapeutic efficacy and to avoid side-toxicity. Cisplatin remains a first line option to treat 20% of all cancer patients and while clearing after 30 min from blood it concentrates in tumor tissues. Here, we demonstrate the use of the platinum-mediated bond cleavage of protected tertiary amides, which can occur in a catalytic manner under bioorthogonal conditions. Protected analogues of cytotoxic drugs 5-fluorouracil (5-FU) and monomethyl auristatin E (MMAE) were successfully activated using non-toxic amounts of platinum salts in cells. An otherwise fully stable and non-internalizing ADC built using a bifunctional linker featuring a tertiary amide protected MMAE was also bioorthogonally decaged in the presence of platinum salts for extracellular drug release. Finally, cisplatin-mediated activation of a prodrug 5-FU was shown in a colorectal zebrafish xenograft model leading to a significant tumor reduction. Considering cisplatin’s continued use as a first-choice treatment for many solid cancers and especially in colorectal cancer, we anticipate that our platinum-mediated decaging strategy will enhance cancer therapy by allowing tumor specific prodrug activation.</p>

scholarly journals Dinuclear manganese alkoxide complexes as catalysts for C–N bond cleavage of simple tertiary N,N-dialkylamides to give esters

2019 ◽  
Vol 10 (10) ◽  
pp. 2860-2868 ◽  
Author(s):  
Haruki Nagae ◽  
Takahiro Hirai ◽  
Daiki Kato ◽  
Shusei Soma ◽  
Shin-ya Akebi ◽  
...  
Keyword(s):  
Chemical Transformation ◽  
Bond Cleavage ◽  
Lone Pair ◽  
Organic Reactions ◽  
Reaction Conditions ◽  
Amide Bonds ◽  
Nitrogen Lone Pair ◽  
Tertiary Amides ◽  
Strong Acids

Amide bonds are stable due to the resonance between the nitrogen lone pair and the carbonyl moiety, and therefore the chemical transformation of amides, especially tertiary amides, involving C–N bond fission is considered one of the most difficult organic reactions, unavoidably requiring harsh reaction conditions and strong acids or bases.

scholarly journals Esterification of Tertiary Amides by Alcohols Through C−N Bond Cleavage over CeO 2

ChemCatChem ◽  
2018 ◽  
Vol 11 (1) ◽  
pp. 15-15
Author(s):  
Takashi Toyao ◽  
Md. Nurnobi Rashed ◽  
Yoshitsugu Morita ◽  
Takashi Kamachi ◽  
S. M. A. Hakim Siddiki ◽  
...  
Keyword(s):  
Bond Cleavage ◽  
Tertiary Amides

Cu-catalyzed aerobic oxidative amidation of aryl alkyl ketones with azoles to afford tertiary amides via selective C–C bond cleavage

2015 ◽  
Vol 2 (7) ◽  
pp. 765-770 ◽  
Author(s):  
Wen Ding ◽  
Qiuling Song
Keyword(s):  
Molecular Oxygen ◽  
Bond Cleavage ◽  
Alkyl Groups ◽  
Aryl Ketones ◽  
Oxidative Amidation ◽  
Tertiary Amides ◽  
Long Chain

Chemoselective cleavage of the C(CO)–C(alkyl) bond in aryl ketones leading to azole amides is disclosed. Aryl ketones with a variety of long-chain alkyl groups have been demonstrated to be active substrates and mechanism studies suggested that molecular oxygen serves both as an oxidant and a reactant in this strategy.

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