C:Corrosive;
110-91-8Relevant articles and documents
Selective electrochemical deprotection of cinnamyl ethers, esters, and carbamates
Hansen, Jeff,Freeman, Stanley,Hudlicky, Tomas
, p. 1575 - 1578 (2003)
Electrochemical deprotection of the cinnamyl moiety from ethers, esters, and carbamates was studied with the focus on O- versus N- selectivity as well as selectivity over allyl or benzyl systems.
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Erickson,Sander
, p. 2086,2088 (1972)
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Experimental investigations of thermal stability of some morpholinecarbamic acid complexes of copper(II) and zinc(II)
Kalia, Shashi B.,Kumar, Rajesh,Bharti, Monika,Christopher
, p. 1291 - 1306 (2017)
Some new carbamates, viz. M(MorphcbmH)2X2 (MorphcbmH?=?morpholinecarbamic acid, M?=?Cu, X?=?Cl, ClO4,NO3; M?=?Zn, X?=?Cl, ClO4, NO3, CH3COO and X2?=?SO4), h
Kinetics and mechanism of large rate enhancement in an acidic aqueous cleavage of the tertiary amide bond of N-(2-methoxyphenyl)-N′-morpholinophthalamide (1)
Sim, Yoke-Leng,Ariffin, Azhar,Khan, M. Niyaz
, p. 178 - 182 (2008)
The rate of conversion of 1 to N-(2-methoxyphenyl)phthalimide (2) within [HCl] range 5.0 × 10-3-1.0 M at 1.0 M ionic strength (by NaCl) reveals the presence of both uncatalyzed and specific acid-catalyzed kinetic terms in the rate law. Intramolecular carboxamide group-assisted cleavage of amide bond of 1 reveals rate enhancement of much larger than 106-fold compared to the expected rate of analogous intermolecular reaction.
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Hampton,Pollard
, p. 2338 (1936)
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Cooperative reactivity in photogenerated radical ion pairs: Photofragmentation of amino ketones
Bergmark, William R.,Whitten, David G.
, p. 4042 - 4043 (1990)
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Infrared studies of amine, pyridine, and phosphine derivatives of tungsten hexacarbonyl
Angelici, Robert J.,Malone, Mary Diana
, p. 1731 - 1736 (1967)
Seventeen complexes, LW(CO)5, where L = amine, pyridine, or phosphine, have been prepared and examined in the C-O stretching region of their infrared spectra. The C-O stretching frequencies and force constants in the amine, pyridine, and phosphine series decrease as the basicity of L increases, and the magnitude of this decrease is virtually the same for all three groups of ligands. The results suggest that W-L π bonding, even for the phosphines, need not be invoked to explain the C-O stretching frequency shifts in these metal carbonyl complexes.
The pyridoxamine action on Amadori compounds: A reexamination of its scavenging capacity and chelating effect
Adrover, Miquel,Vilanova, Bartolome,Frau, Juan,Munoz, Francisco,Donoso, Josefa
, p. 5557 - 5569 (2008)
Amadori compounds act as precursors in the formation of advanced glycation end products (AGEs) by non-enzymatic protein glycation, which are involved in ensuing protein damage. Pyridoxamine is a potent drug against protein glycation, and can act on several pathways in the glycation process. Nevertheless, the pyridoxamine inhibition action on Amadori compounds oxidation is still unclear. In this work, we have studied the Schiff base formation between pyridoxamine and various Amadori models at pH 7.4 at 37 °C in the presence of NaCNBH3. We detected an adduct formation, which suggests that pyridoxamine reacts with the carbonyl group in Amadori compounds. The significance of this mechanism is tested by comparison of the obtained kinetics rate constants with that obtained for 4-(aminomethyl)-pyridine, a structural analogue of pyridoxamine without post-Amadori action. We also study the chelating effect of pyridoxamine on metal ions. We have determined the complexation equilibrium constants between pyridoxamine, N-(1-deoxy-d-fructos-1-yl)-l-tryptophan, aminoguanidine, and ascorbic acid in the presence of Zn2+. The results show that the strong stability of pyridoxamine complexes is the key in its post-Amadori inhibition action. On the other hand results explain the lack of inhibition of aminoguanidine (a glycation inhibitor) in the post-Amadori reactions.
The benzyl can be selectively removed by visible light or near visible light. Method for protecting allyl and propargyl group
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Paragraph 0024, (2021/10/16)
The invention provides a method for selectively removing benzyl, allyl and propargyl protecting groups by visible light or near visible light, namely a substrate containing benzyl, allyl or propargyl protecting groups. The method has the advantages of simple operation, safe and clean visible light or near visible light as excitation conditions, cheap and easily available reagents, high reaction yield, high reaction chemistry and regional selectivity, and is suitable for selective removal of benzyl, allyl and propargyl protecting groups in various substrates.
Platinum-Triggered Bond-Cleavage of Pentynoyl Amide and N-Propargyl Handles for Drug-Activation
Oliveira, Bruno L.,Stenton, Benjamin J.,Unnikrishnan,De Almeida, Cátia Rebelo,Conde, Jo?o,Negr?o, Magda,Schneider, Felipe S.S.,Cordeiro, Carlos,Ferreira, Miguel Godinho,Caramori, Giovanni F.,Domingos, Josiel B.,Fior, Rita,Bernardes, Gon?alo J. L.
supporting information, p. 10869 - 10880 (2020/07/04)
The ability to create ways to control drug activation at specific tissues while sparing healthy tissues remains a major challenge. The administration of exogenous target-specific triggers offers the potential for traceless release of active drugs on tumor sites from antibody-drug conjugates (ADCs) and caged prodrugs. We have developed a metal-mediated bond-cleavage reaction that uses platinum complexes [K2PtCl4 or Cisplatin (CisPt)] for drug activation. Key to the success of the reaction is a water-promoted activation process that triggers the reactivity of the platinum complexes. Under these conditions, the decaging of pentynoyl tertiary amides and N-propargyls occurs rapidly in aqueous systems. In cells, the protected analogues of cytotoxic drugs 5-fluorouracil (5-FU) and monomethyl auristatin E (MMAE) are partially activated by nontoxic amounts of platinum salts. Additionally, a noninternalizing ADC built with a pentynoyl traceless linker that features a tertiary amide protected MMAE was also decaged in the presence of platinum salts for extracellular drug release in cancer cells. Finally, CisPt-mediated prodrug activation of a propargyl derivative of 5-FU was shown in a colorectal zebrafish xenograft model that led to significant reductions in tumor size. Overall, our results reveal a new metal-based cleavable reaction that expands the application of platinum complexes beyond those in catalysis and cancer therapy.
Rational selection of co-catalysts for the deaminative hydrogenation of amides
Artús Suàrez, Lluís,Jayarathne, Upul,Balcells, David,Bernskoetter, Wesley H.,Hazari, Nilay,Jaraiz, Martín,Nova, Ainara
, p. 2225 - 2230 (2020/03/10)
The catalytic hydrogenation of amides is an atom economical method to synthesize amines. Previously, it was serendipitously discovered that the combination of a secondary amide co-catalyst with (iPrPNP)Fe(H)(CO) (iPrPNP = N[CH2CH2(PiPr2)]2-), results in a highly active base metal system for deaminative amide hydrogenation. Here, we use DFT to develop an improved co-catalyst for amide hydrogenation. Initially, we computationally evaluated the ability of a series of co-catalysts to accelerate the turnover-limiting proton transfer during C-N bond cleavage and poison the (iPrPNP)Fe(H)(CO) catalyst through a side reaction. TBD (triazabicyclodecene) was identified as the leading co-catalyst. It was experimentally confirmed that when TBD is combined with (iPrPNP)Fe(H)(CO) a remarkably active system for amide hydrogenation is generated. TBD also enhances the activity of other catalysts for amide hydrogenation and our results provide guidelines for the rational design of future co-catalysts.
