638-37-9Relevant academic research and scientific papers
Epoxide-opening cascades triggered by a Nicholas reaction: Total synthesis of teurilene
Rodríguez-L?pez, Julio,Pinacho Cris?stomo, Fernando,Ortega, Nuria,L?pez-Rodríguez, Matías,Martín, Víctor S.,Martín, Tomás
, p. 3659 - 3662 (2013)
Natural inspiration: Based on the biosynthesis of squalene-derived polyethers, a total synthesis of teurilene is described. The carbocation formation in the Nicholas reaction serves to control the initiation of a polyepoxide ring-opening cascade. The three furan rings present in teurilene were obtained in excellent yield in one step. Boc=tert-butoxycarbonyl, TMS=trimethylsilyl. Copyright
Radiosynthesis of tritium-labeled novel nitromethylene neonicotinoids compounds with NaB3H4
Li, Chao,Xu, Xiao-Yong,Li, Ju-Ying,Ye, Qing-Fu,Li, Zhong
, p. 256 - 259 (2011)
Paichongding and Cycloxaprid are two novel neonicotinoids with good industrialization prospects for their high activity against imidacloprid- resistant pest. In this paper, the radiosynthesis of [3H 2]-Paichongding and [3H2]-Cycloxaprid was achieved using a NaB3H4 reduction. The title compounds were obtained with chemical purities of 98.7 and 98.4%, and radiochemical purities of 97.3 and 98.6%, respectively. The labeled compounds could be used as radiotracers for further study of metabolism and toxicology. Copyright
2:2 condensation products from the reaction of N-substituted 1,2-diaminoethanes and 1,3-diaminopropanes with succinaldehyde and glutaraldehyde
Okawara, Tadashi,Okamoto, Yoshinari,Ehara, Shuji,Yamasaki, Tetsuo,Furukawa, Mitsuru
, p. 2487 - 2493 (1996)
The reaction of N-substituted 1,2-diaminoethanes and 1,3-diaminopropanes (1) with succinaldehyde (2) and glutaraldehyde (9) in water gave the 2:2 condensation products (4 and 10).
Synthetic studies on amphidinolides C and F: synthesis of the C18-C29 segment of amphidinolide F
Armstrong, Alan,Pyrkotis, Constantina
, p. 3325 - 3328 (2009)
The C18-C29 segment of amphidinolide F is synthesised in 12 steps from 1,4-butanediol. Key steps include a mono-Sharpless dihydroxylation of a dienoate, iodocyclisation to construct the trans-THF ring and an E-selective Wittig reaction to introduce the C25-C26 olefin.
Diastereoselective Synthesis of Cyclic Five-Membered trans,trans-Configured Nitrodiols by Double Henry Reaction of 1,4-Dialdehydes
Fr?hlich, Janine,Lehmkuhl, Kirstin,Fr?hlich, Roland,Wünsch, Bernhard
, p. 589 - 594 (2015)
Conformationally constrained perhydroquinoxalines 4 show high κ receptor affinity, selectivity over related receptors and full agonistic activity. Since the κ affinity can be correlated with the dihedral angle of the ethylenediamine pharmacophore (4a: 55°/71°), the dihedral angles of the postulated cyclopentane derivative 5a (73°/84°) and indane derivative 6a (77°/81°) were calculated. The first step of the synthesis represents a double Henry reaction of 1,4-dialdehydes 8 and 10 with nitromethane, leading predominantly to the trans,trans-configured nitrodiols 9 and 11. X-ray crystal structure analyses of 9 and 11 led to dihedral angles O2N-C-C-OH of 73.4 and 88.3°, respectively, which reflect the calculated dihedral angles of the hypothesized final products 5a and 6a. Since κ receptor affinity can be correlated with the dihedral angle of ethylenediamine pharmacophores, the dihedral angles of the postulated cyclopentane derivative 5a (73°/84°) and indane derivative 6a (77°/81°) were calculated. X-ray crystal structure analyses of the synthesized compounds 9 and 11 led to dihedral angles of 73.4 and 88.3°, respectively, reflecting the calculated dihedral angles of the hypothesized final products 5a and 6a.
Seven-membered azabridged neonicotinoids: Synthesis, crystal structure, insecticidal assay, and molecular docking studies
Xu, Renbo,Luo, Ming,Xia, Rui,Meng, Xiaoqing,Xu, Xiaoyong,Xu, Zhiping,Cheng, Jiagao,Shao, Xusheng,Li, Houju,Li, Zhong
, p. 11070 - 11079 (2014)
To study the influence of the ring sizes, 37 novel seven-membered azabridged neonicotinoid analogues were synthesized by reactions of nitromethylene analogues, succinaldehyde, and aniline hydrochlorides. Most of the title compounds presented higher insecticidal activities than that of imidacloprid (IMI), cycloxaprid (CYC), and eight-membered compounds against cowpea aphid (Aphis craccivora), armyworm (Pseudaletia separata Walker), and brown planthopper (Nilaparvata lugens), which indicated that introducing the structure of a seven-membered azabridge could significantly improve the insecticidal activities of neonicotinoid analogues. Docking study and binding mode analysis also revealed that introducing methyl group into position 2 of phenyl ring could increase the hydrophobic interactions with receptor, which implied that position 2 might be the key site to get high insecticidal compounds.
Reoptimization of the Organocatalyzed Double Aldol Domino Process to a Key Enal Intermediate and Its Application to the Total Synthesis of Δ12-Prostaglandin J3
Pel?s, Andrejs,Gandhamsetty, Narasimhulu,Smith, James R.,Mailhol, Damien,Silvi, Mattia,Watson, Andrew J. A.,Perez-Powell, Isabel,Prévost, Sébastien,Schützenmeister, Nina,Moore, Peter R.,Aggarwal, Varinder K.
, p. 9542 - 9545 (2018)
Re-investigation of the l-proline catalyzed double aldol cascade dimerization of succinaldehyde for the synthesis of a key bicyclic enal intermediate, pertinent in the field of stereoselective prostaglandin synthesis, is reported. The yield of this process has been more than doubled, from 14 % to a 29 % isolated yield on a multi-gram scale (32 % NMR yield), through conducting a detailed study of the reaction solvent, temperature, and concentration, as well as a catalyst screen. The synthetic utility of this enal intermediate has been further demonstrated through the total synthesis of Δ12-prostaglandin J3, a compound with known anti-leukemic properties.
Novel small-molecule hybrid-antibacterial agents against s. Aureus and mrsa strains
Gehrmann, Robin,Hertlein, Tobias,Hilgeroth, Andreas,Hopke, Elisa,Lalk, Michael,Ohlsen, Knut
, (2021/12/29)
Ongoing resistance developments against antibiotics that also affect last-resort antibiotics require novel antibacterial compounds. Strategies to discover such novel structures have been dimerization or hybridization of known antibacterial agents. We found novel antibacterial agents by dimerization of indols and hybridization with carbazoles. They were obtained in a simple one-pot reaction as bisindole tetrahydrocarbazoles. Further oxidation led to bisindole carbazoles with varied substitutions of both the indole and the carbazole scaffold. Both the tetrahydrocarbazoles and the carbazoles have been evaluated in various S. aureus strains, including MRSA strains. Those 5-cyano substituted derivatives showed best activities as determined by MIC values. The tetrahydrocarbazoles partly exceed the activity of the carbazole compounds and thus the activity of the used standard antibiotics. Thus, promising lead compounds could be identified for further studies.
Direct catalytic synthesis of β-(C3)-substituted pyrroles: A complementary addition to the Paal-Knorr reaction
Pawar, Amol Prakash,Yadav, Jyothi,Mir, Nisar Ahmad,Iype, Eldhose,Rangan, Krishnan,Anthal, Sumati,Kant, Rajni,Kumar, Indresh
supporting information, p. 251 - 254 (2021/01/13)
The synthesis of β-(C3)-functionalized pyrroles is a challenging task and requires a multistep protocol. An operationally simple direct catalytic synthesis of β-substituted pyrroles has been developed. This one-pot multicomponent method combined aqueous succinaldehyde as 1,4-dicarbonyl, primary amines, and isatins to access hydroxyl-oxindole β-tethered pyrroles. Direct synthesis of the β-substituted free NH-pyrrole is the central intensity of this work. DFT-calculations and preliminary mechanism investigation support the possible reaction pathway. This journal is
The structure modification of seven-membered aza-brigded neonicotinoids in order to investigate their impact on honey bees
Cao, Xiaofeng,Chen, Xi,Chen, Yuce,Li, Zhong,Xu, Xiaoyong
, p. 835 - 844 (2021/05/29)
In order to explore the relationship between the structure and the toxicity to honey bees of seven-membered aza-bridged neonicotinoids, 16 novel seven-membered aza-bridged neonicotinoid analogues are synthesized by replacing the pyridine ring, and changing the substituents on the pyridine ring, the electron-withdrawing group NO2 and the imidazole ring of our previously developed aza-bridged neonicotinoid 1-[(6-chloropyridin-3-yl)methyl)]-10-(2,5-dimethylphenyl)-9-nitro-2,3,5,6,7,8-hexahydro-1H-5,8-epiminoimidazo azepine (C-29). The insecticidal bioactivities against cowpea aphid (Aphis craccivora) and the bee toxicities of these compounds are tested. Some of the title compounds present good insecticidal activities against cowpea aphid. The results also show that some of the title compounds exhibit lower bee toxicity than that of C-29 and imidacloprid. This suggests that changing the substituents on the neonicotinoids can influence the toxicity toward honey bees of these analogues.
