- Design, synthesis and bioactivity evaluation of novel thioether derivatives containing a sulfonohydrazide moiety
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A series of novel thioether derivatives containing a sulfonohydrazide moiety were synthesized and determined using 1H NMR, 13C NMR, HRMS, and elemental analysis. Their in vitro antibacterial activities against Xanthomonas oryzae pv.
- Li, Pei,Zhou, Junliang,Liu, Yan,Wang, Xiang
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p. 976 - 980
(2020/07/03)
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- COMPOSITIONS, SYNTHESIS, AND METHODS OF USING PHENYLCYCLOALKYLMETHYLAMINE DERIVATIVES
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The present invention provides novel phenylcycloalkylmethylamme derivatives, and methods of preparing phenylcycloalkylmethylamme derivatives. The present invention also provides methods of using phenylcycloalkylmethylamme derivatives and compositions of phenylcycloalkylmethylamme derivatives. The pharmaceutical compositions of the compounds of the present invention can be used for treating and/or preventing obesity and obesity related co- morbid indications and depression and depression related co-morbid indications.
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Page/Page column 56
(2013/07/19)
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- Iron(III) corroles and porphyrins as superior catalysts for the reactions of diazoacetates with nitrogen- or sulfur-containing nucleophilic substrates: Synthetic uses and mechanistic insights
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A thorough mechanistic investigation has been performed on the reactions of primary and secondary amines with diazoacetates, which proceed uniquely quickly and efficiently when catalyzed by iron(III) corroles and porphyrins. Two major differences in relation to other metal-based catalysts are that the iron complexes are not poisoned by excess amine and that metal-carbene intermediates are apparently not involved in the reaction pathway. The results instead point towards nitrogen ylide intermediates formed by nucleophilic attack of the amines on diazoacetate-coordinated iron complexes. Nitrogen ylides are also formed when allyl- and propargylsubstituted tertiary amines react with diazoacetates, a scenario that smoothly leads to 2,3-rearrangement reaction products with catalytic amounts of the iron(III) complexes. Similar findings regarding the superiority of the iron-(III) complexes (in terms of catalyst loading, chemical yields, and reaction conditions) were obtained with thiols (S-H insertion) and sulfides (2,3-rear-rangement reactions), which suggest similar mechanisms operate in these cases.
- Aviv, Iris,Gross, Zeev
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scheme or table
p. 3995 - 4005
(2009/05/26)
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- Studies on umami taste. Synthesis of new guanosine 5′-phosphate derivatives and their synergistic effect with monosodium glutamate
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A number of N2-alkyl and N2-acyl derivatives of guanosine 5′-phosphate (GMP) have been synthesized and tested for their synergistic effect with monosodium L-glutamate (MSG), the prototypical substance imparting umami taste to savory-based foods. Capacities to enhance the taste intensity of MSG (γ values) were estimated through subjective comparisons of MSG/nucleotide mixtures in water with appropriate solutions of MSG alone. Assuming β = γ[nucleotide]/γ[IMP], β values of the N 2-substituted GMPs were found in the range 1.2-5.7. Such values appear to be related to the chain length of the substituent in the 2-position of the purine nucleus and dependent on the replacement of a CH2 group with an S atom and/or with an α-CO group. These findings indicate that the exocyclic NHR group of the guanine moiety is actively implicated in the synergism between GMP derivatives and MSG. Theoretical calculations suggest that an anti conformation is probably assumed by ribonucleotide molecules interacting with umami receptors.
- Cairoli, Paola,Morelli, Carlo F.,Speranza, Giovanna,Manitto, Paolo,Pieraccini, Stefano,Sironi, Maurizio
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supporting information; scheme or table
p. 1043 - 1050
(2009/05/08)
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- N-ALKYNYL-2- (SUBSTITUTED ARYLOXY) ALKYLTHIOAMIDE DERIVATIVES AS FUNGICIDES
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Fungicidal compounds of the general formula (1), wherein Ar is a group of the formula (A), (B1), (B2) or (C), or Ar is a 5- or 6-linked group of the formula (D1) or (D2); and R1, R2, R3, R4, R5, n, A1, A2, A3, A4, A5, Ka, Kb, L, M, V, W, X,Y and Z have the definitions given in claim 1.
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- The photochemistry of sulfur analogues of dialkyldiazomalonates
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Laser flash photolysis studies (LFP) of O,S-diethylmonothiodiazomalonate (1) and S,S-dietrryldithiodiazomalonate (2) in 1,1,2-trichlorotrifluoroethane (Freon-113) were consistent with the trapping of an intermediate with λmax = 425 nm, attributed, in the LFP of 1, to that of ylide 10, formed from the reaction of singlet O,S-carboethoxythioethoxycarbene (9) with pyridine. The deduced lifetime of both singlet O,S-dicarboethoxycarbene (9) and S,S-dicarbothioethoxycarbene (13) are essentially the same in Freon-113, but compared to dicarbomethoxycarbene 14, the lifetimes of 9 and 13 were found to be about six times shorter. The LFP studies, in addition to calculations at the B3LYP/6-31 G* level of theory, provide an explanation for the effect of sulfur perturbation that shortens the carbene lifetimes, as well as an explanation for the exclusive migration of the SEt group to ultimately form 5 upon light (300 nm) induced nitrogen extrusion and Wolff rearrangement of 1 in EtOH.
- Snoonian, John R.,Platz, Matthew S.
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p. 9276 - 9280
(2007/10/03)
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- 4-sulfenyl-2-carbamoyl-4-isoxazolin-3-ones: Biological isostere to 4- chloro-2-carbamoyl-4-isoxazolin-3-ones
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4-Sulfenyl-2-carbamoyl-4-isoxazolin-3-ones (4) were designed on the basis of biological isosterism and prepared in four steps. Some of these compounds showed sufficient pre-emergent herbicidal activities against various kinds of weeds. Among the synthesiz
- Kudo, Noriaki,Yoneda, Takamitsu,Sato, Kazuo,Honma, Toyokuni,Sugai, Soji
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p. 509 - 515
(2007/10/03)
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- Organic reactions catalyzed by methylrhenium trioxide: Reactions of ethyl diazoacetate and organic azides
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Methylrhenium trioxide (CH3ReO3 or MTO) catalyzes several classes of reactions of ethyl diazoacetate, EDA. It is the first high valent oxo complex for carbene transfer. Under mild conditions and in the absence of other substrates, EDA was converted to a 9:1 mixture of diethyl maleate and diethyl fumarate. In the presence of alcohols, α-alkoxy ethyl acetates were obtained in good yield. The yields dropped for the larger and more branched alcohols, the balance of material being diethyl maleate and fumarate. An electron-donating group in the para position of phenols favors the formation of α-phenoxy ethyl acetates. The use of EDA to form α-thio ethyl acetates and N-substituted glycine ethyl esters, on the other hand, is hardly affected by the size or structure of the parent thiol or amine, with all of these reactions proceeding in high yield. MTO-catalyzed cycloaddition reactions occur between EDA and aromatic imines, olefins, and carbonyl compounds. Three-membered ring products are formed: aziridines, cyclopropanes, and epoxides, respectively. The reactions favor the formation of trans products, and provide a convenient route for the preparation of aziridines. Intermediate carbenoid and nitrenoid species have been proposed. In the presence of an oxygen source such as an epoxide, ethyl diazoacetate and azibenzil are converted to an oxalic acid monoethyl ester and tobenzil; at the same time the epoxide was converted to an olefin. These results provide further support for the proposed intermediate, a cyclic species containing Re, O, and CHCO2Et (or, occasionally, CPhC(O)Ph)in a three-membered ring.
- Zhu, Zuolin,Espenson, James H.
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p. 9901 - 9907
(2007/10/03)
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