502-83-0Relevant articles and documents
Docking model of the nicotinic acetylcholine receptor and nitromethylene neonicotinoid derivatives with a longer chiral substituent and their biological activities
Nagaoka, Hikaru,Nishiwaki, Hisashi,Kubo, Takuya,Akamatsu, Miki,Yamauchi, Satoshi,Shuto, Yoshihiro
, p. 759 - 769 (2015/02/19)
In the present study, nitromethylene neonicotinoid derivatives possessing substituents that contain a sulfur atom, oxygen atom or aromatic ring at position 5 on the imidazolidine ring were synthesized to evaluate their affinity for the nicotinic acetylcholine receptor (nAChR) and their insecticidal activity against adult female houseflies. Comparing the receptor affinity of the alkylated derivative with the receptor affinity of compounds possessing either ether or thioether groups revealed that conversion of the carbon atom to a sulfur atom did not influence the receptor affinity, whereas conversion to an oxygen atom was disadvantageous for the receptor affinity. The receptor affinity of compounds possessing a benzyl or phenyl group was lower than that of the unsubstituted compound. Analysis of the three-dimensional quantitative structure-activity relationship using comparative molecular field analysis demonstrated that steric hindrance of the receptor should exist around the C3 of an n-butyl group attached at position 5 on the imidazolidine ring. A docking study of the nAChR-ligand model suggested that the ligand-binding region expands as the length of the substituent increases by brushing against the amino acids that form the binding region. The insecticidal activity of the compounds was positively correlated with the receptor affinity by considering log P and the number of heteroatoms, including sulfur and oxygen atoms, in the substituents, suggesting that the insecticidal activity is influenced by the receptor affinity, hydrophobicity, and metabolic stability of the compounds.
A highly stereoselective synthesis of glycidic amides based on a new class of chiral sulfonium salts: Applications in asymmetric synthesis
Sarabia, Francisco,Vivar-García, Carlos,García-Castro, Miguel,García-Ruiz, Cristina,Martín-Gálvez, Francisca,Sánchez-Ruiz, Antonio,Chammaa, Samy
supporting information, p. 15190 - 15201 (2013/01/15)
A new type of chiral sulfonium salts that are characterized by a bicyclic system has been designed and synthesized from α-amino acids. Their corresponding ylides, which were prepared by basic treatment of the sulfonium salts, reacted smoothly with a broad array of simple and chiral aldehydes to provide trans-epoxy amides in reasonable to very good yields and excellent stereoselectivities (>98 %). The obtained epoxy amides were found to be useful as synthetic building blocks. Thus, they were reduced into their corresponding epoxy alcohols and subjected to oxirane-ring-opening reactions with different types of nucleophiles.
An efficient synthesis of (R)-3-aminothiolane
Pan, Xianhua,Tao, Xiaohu,Ruan, Libo,Li, Yiming,Ou, Wenhua,Liu, Feng
experimental part, p. 729 - 730 (2012/03/27)
An efficient synthesis of (R)-3-aminothiolane is described based on a one-pot tandem hydroxyl activation-intramolecular cyclisation of Ts-protected-D-methioninol in the presence of methanesulfonyl chloride/pyridine. Removal of the tosyl group then gave (R)-3-aminothiolane in good yield. (R)-3-Aminothiolane derivatives are important building blocks for the synthesis of biologically active compounds.
A highly efficient methodology of asymmetric epoxidation based on a novel chiral sulfur ylide
Sarabia, Francisco,Chammaa, Samy,Garcia-Castro, Miguel,Martin-Galvez, Francisca
supporting information; experimental part, p. 5763 - 5765 (2010/01/31)
A new type of chiral sulfur ylides has been synthesized and their reactivities against carbonyl compounds tested, showing a high degree of stereoselectivity in the formation of trans epoxy amides under very mild reaction conditions.
Structure-activity relationships of adenosines with heterocyclic N6-substituents
Ashton,Aumann, Kylee M.,Baker, Stephen P.,Schiesser, Carl H.,Scammells, Peter J.
, p. 6779 - 6784 (2008/04/07)
Two series of N6-substituted adenosines with monocyclic and bicyclic N6 substituents containing a heteroatom were synthesized in good yields. These derivatives were assessed for their affinity ([3H]CPX), potency, and intrinsic activity (cAMP accumulation) at the A1 adenosine receptor in DDT1 MF-2 cells. In the monocyclic series, the N6-tetrahydrofuran-3-yl and thiolan-3-yl adenosines (1 and 26, respectively) were found to possess similar activities, whereas the corresponding selenium analogue 27 was found to be more potent. A series of nitrogen containing analogues showed varying properties, N6-((3R)-1-benzyloxycarbonylpyrrolidin-3-yl)adenosine (30) was the most potent at the A1AR; IC50 = 3.2 nM. In the bicyclic series, the effect of a 7-azabicyclo[2.2.1]heptan-2-yl substituent in the N6-position was explored. N6-(7-Azabicyclo[2.2.1]heptan-2-yl)adenosine (38) proved to be a reasonably potent A1 agonist (Ki = 51 nM, IC50 = 35 nM) while further substitution on the 7″-nitrogen with tert-butoxycarbonyl (31, IC50 = 2.5 nM) and 2-bromobenzyloxycarbonyl (34, IC50 = 9.0 nM) gave highly potent A1AR agonists.
DABCO catalyzed reaction of various nucleophiles with activated alkynes leading to the formation of alkenoic acid esters, 1,4-dioxane, morpholine, and piperazinone derivatives
Fan, Ming-Jin,Li, Gao-Qiang,Liang, Yong-Min
, p. 6782 - 6791 (2007/10/03)
The reaction of acids, alcohols, acylamides, 1,2-diols, 1,2-diamines or amino alcohols with activated alkynes catalyzed by 1,4-diazabicyclo[2.2.2]octane (DABCO) was systematically investigated. A series of unsaturated alkenoic acid esters or heterocycles were formed in the reaction of monobasic or dibasic nucleophiles in excellent yields, respectively.
Bifunctional bis(oxazolines) as potential ligands in catalytic asymmetric reactions
Hanessian, Stephen,Jnoff, Eric,Bernstein, Noemy,Simard, Michel
, p. 306 - 313 (2007/10/03)
C2-symmetrical bis(oxazoline) ligands bearing pendant alkylthio ether groups were synthesized, and the structures of Cu complexes were determined by single crystal X-ray diffraction. The potential utility in catalysis was shown in the asymmetric addition of methyllithium to an aromatic aldimine, which resulted in a mixture of products with an enantiomeric excess of 68%.
Enantioselective Synthesis of Non-Natural Aromatic α-Amino Acids
Krebs, Andreas,Ludwig, Verena,Pfizer, Jose,Duerner, Gerd,Goebel, Michael W.
, p. 544 - 553 (2007/10/03)
We present two complementary methods for the stereoselective synthesis of non-natural α-amino acids with aromatic or heteroaromatic side chains. One approach is based on the chemical transformation of methionine, whereas the other applies the stereoselective Myers alkylation of glycine. The resulting product types differ in the linker length between glycine and the aromatic substituent. Since methionine and pseudoephedrine are available in both absolute configurations, R- or S-configured enantiopure amino acids with either C2 or C3 linkers can be obtained on gram scales. In each case the key step of the synthesis is hydroboration of the unsaturated building blocks 9 and 17, followed by palladium-catalyzed Suzuki cross-coupling with aryl halides. Attention must in certain cases be paid to the stereochemical integrity when basic Suzuki conditions are applied. Our initial difficulties are reported as well as the final "racemization-proof" procedures. The protecting groups chosen for the α-amino acids should be compatible with solid-phase peptide synthesis. This was confirmed by the successful synthesis of a series of tripeptides.
SYNTHESIS OF THE SERINE EQUIVALENT, (2R) AND (2S)-AMINO-3-BUTENOL DERIVATIVES. SYNTHETIC APPROACHES TO THE METAL CHELATING POLY-AMINO ACID, "ASPERGILLOMARASMINE A"
Ohfune, Yasufumi,Kurokawa, Natsuko
, p. 1071 - 1074 (2007/10/02)
Chiral synthons, equivalent to the C3 amino acid serine, were synthesized in both (2R) and (2S) form from D or L-methionine respectively; Utilization of this synthon in the construction of metal chelating poly-amino acid aspergillomarasmine A skeleton is presented.
