26107-82-4Relevant articles and documents
Design, Synthesis, and Study of the Insecticidal Activity of Novel Steroidal 1,3,4-Oxadiazoles
Bai, Hangyu,Jiang, Weiqi,Li, Qi,Li, Tian,Ma, Shichuang,Shi, Baojun,Wu, Wenjun
, p. 11572 - 11581 (2021/10/12)
A series of novel steroidal derivatives with a substituted 1,3,4-oxadiazole structure was designed and synthesized, and the target compounds were evaluated for their insecticidal activity against five aphid species. Most of the tested compounds exhibited potent insecticidal activity against Eriosoma lanigerum (Hausmann), Myzus persicae, and Aphis citricola. Compounds 20g and 24g displayed the highest activity against E. lanigerum, showing LC50 values of 27.6 and 30.4 μg/mL, respectively. Ultrastructural changes in the midgut cells of E. lanigerum were detected by transmission electron microscopy, indicating that these steroidal oxazole derivatives might exert their insecticidal activity by destroying the mitochondria and nuclear membranes in insect midgut cells. Furthermore, a field trial showed that compound 20g exhibited effects similar to those of the positive controls chlorpyrifos and thiamethoxam against E. lanigerum, reaching a control rate of 89.5% at a dose of 200 μg/mL after 21 days. We also investigated the hydrolysis and metabolism of the target compounds in E. lanigerum by assaying the activities of three insecticide-detoxifying enzymes. Compound 20g at 50 μg/mL exhibited inhibitory action on carboxylesterase similar to the known inhibitor triphenyl phosphate. The above results demonstrate the potential of these steroidal oxazole derivatives to be developed as novel pesticides.
Synthesis, fungicidal activity, and 3D-QSAR of tetrazole derivatives containing phenyloxadiazole moieties
Li, Yi-Tao,Yao, Wen-Qiang,Zhou, Si,Xu, Jun-Xing,Lu, Hui,Lin, Jian,Hu, Xiao-Yun,Zhang, Shao-Kai
supporting information, (2021/01/11)
In an effort to discover new agents with good fungicidal activities against CDM (cucumber downy mildew), a series of tetrazole derivatives containing phenyloxadiazole moieties were designed and synthesized. The EC50 values for fungicidal activities against CDM were determined. Bioassay results indicated that most synthesized compounds exhibited potential in vivo fungicidal activity against CDM. A CoMFA (comparative molecular field analysis) model based on the bioactivity was developed to identify some primary structural quality for the efficiency. The values of q2 and r2 for the established model were 0.791 and 0.982 respectively, which reliability and predict abilities were verified. Three analogues (q3, q4, q5) were designed and synthesized based on the model. All these compounds exhibited significant fungicidal activity on CDM with the EC50 of 1.43, 1.52, 1.77 mg·L?1. This work could provide a useful instruction for the further structure optimization.
AMINO ALCOHOL DERIVATIVE, PHARMACEUTICAL COMPOSITION AND APPLICATION THEREOF
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Paragraph 0253; 0255; 0256, (2021/11/13)
The present invention belongs to the field of medicine, and specifically discloses an amino alcohol derivative represented by Formula I, a pharmaceutically acceptable salt, solvate, polymorph or prodrug thereof. In addition, the present invention also discloses a pharmaceutical composition comprising the above substances, and a use of the substance in the preparation of a medicament for the prevention and treatment of an immune inflammatory disease, or a disease or condition associated with immunological competence such as multiple sclerosis, ALS, CIDP, systemic lupus erythematosus, rheumatoid arthritis, ulcerative colitis, psoriasis, polymyositis, etc.
Antinociceptive and cytotoxic activity of opioid peptides with hydrazone and hydrazide moieties at the C-terminus
Bochynska-Czyz, Marta,Dyniewicz, Jolanta,Kosson, Piotr,Lipinski, Piotr F. J.,Matalinska, Joanna,Misicka, Aleksandra
, (2020/09/16)
In the present contribution, we analyze the influence that C-terminal extension of short opioid peptide sequences by organic fragments has on receptor affinity, in vivo analgesic activity, and antimelanoma properties. The considered fragments were based on either N-acylhydrazone (NAH) or N0-acylhydrazide motifs combined with the 3,5-bis(trifluoromethyl)phenyl moiety. Eleven novel compounds were synthesized and subject to biological evaluation. The analyzed compounds exhibit a diversified range of affinities for the μ opioid receptor (MOR), rather low δ opioid receptor (DOR) affinities, and no appreciable neurokinin-1 receptor binding. In three out of four pairs, N-acylhydrazone-based derivatives bind MOR better than their N’-acylhydrazide counterparts. The best of the novel derivatives have similar low nanomolar MOR binding affinity as the reference opioids, such as morphine and biphalin. The obtained order of MOR affinities was compared to the results of molecular docking. In vivo, four tested compounds turned out to be relatively strong analgesics. Finally, the NAH-based analogues reduce the number of melanoma cells in cell culture, while their N0-acylhydrazide counterparts do not. The antimelanoma properties are roughly correlated to the lipophilicity of the compounds.
A general and efficient entry to asymmetric tetrazines for click chemistry applications
Wang, Danzhu,Chen, Weixuan,Zheng, Yueqin,Dai, Chaofeng,Wang, Lifang,Wang, Binghe
, p. 171 - 177 (2013/09/02)
The importance of click chemistry is widely recognized. Among all the known click reactions, those involving tetrazines represent the fastest click reactions reported and are generating a great deal of interest. However, there is no efficient entry to asymmetric tetrazines and those with strong electron withdrawing groups, which limits the development of this field. Herein, we report a general and efficient entry to asymmetric tetrazines with strongly electron withdrawing groups.
Synthesis of bipolar charge transporting block copolymers and characterization for organic light-emitting diode
Tsuchiya, Kousuke,Kasuga, Hidemasa,Kawakami, Akira,Taka, Hideo,Kita, Hiroshi,Ogino, Kenji
experimental part, p. 1461 - 1468 (2011/02/25)
A series of hole and electron transporting random and block copolymers consisting of triphenylamine moiety as a hole transporting unit and oxadiazole moiety as an electron transporting unit have been prepared via a nitroxide mediated radical polymerization. Oxadiazole monomers with t-butyl or trifluoromethyl groups, 2 and 7, respectively, were used for copolymerization. Photoluminescent measurements of polymers revealed that the formation of the exciplex between triphenylamine and oxadiazole units tends to occur in the order of random copolymers, block copolymers, and polymer blends, implying phase-separated morphologies in block or blend systems. The polymers were applied for OLED devices, and we found that the morphology in the polymer layer critically affected device performance. The block copolymer comprising hole and electron transporting units with the composition of 14/86 showed the highest external quantum efficiency over 10%.
Potent oxadiazole CGRP receptor antagonists for the potential treatment of migraine
Nichols, Paula L.,Brand, Jonathan,Briggs, Michael,D'Angeli, Mathilde,Farge, Jennifer,Garland, Stephen L.,Goldsmith, Paul,Hutchings, Rio,Kilford, Ian,Li, Ho Y.,MacPherson, David,Nimmo, Fiona,Sanderson, Francis Dominic,Sehmi, Sanjeet,Shuker, Nicola,Skidmore, John,Stott, Michael,Sweeting, Jennifer,Tajuddin, Hasmi,Takle, Andrew K.,Trani, Giancarlo,Wall, Ian D.,Ward, Robert,Wilson, David M.,Witty, David
scheme or table, p. 1368 - 1372 (2010/07/02)
A pharmacophore model was built, based on known CGRP receptor antagonists, and this was used to aid the identification of novel leads. Analogues were designed, modelled and synthesised which incorporated alternative 'LHS' fragments linked via either an amide or urea to a privileged 'RHS' fragment commonly found in CGRP receptor antagonists. As a result a novel series of oxadiazole CGRP receptor antagonists has been identified and the subsequent optimisation to enhance both potency and bioavailability is presented.
3-[(5-Chloro-2-hydroxyphenyl)methyl]-5-[4-(trifluoromethyl)phenyl]-1,3, 4-oxadiazol-2(3H)-one, BMS-191011: Opener of large-conductance Ca 2+-activated potassium (maxi-K) channels, identification, solubility, and SAR
Romine, Jeffrey L.,Martin, Scott W.,Meanwell, Nicholas A.,Gribkoff, Valentin K.,Boissard, Christopher G.,Dworetzky, Steven I.,Natale, Joanne,Moon, Sandra,Ortiz, Astrid,Yeleswaram, Swamy,Pajor, Lorraine,Gao, Qi,Starrett Jr., John E.
, p. 528 - 542 (2007/10/03)
Compound 8a (BMS-191011), an opener of the cloned large-conductance, Ca2+-activated potassium (maxi-K) channel, demonstrated efficacy in in vivo stroke models, which led to its nomination as a candidate for clinical evaluation. Its maxi-K channel opening properties were consistent with its structural topology, being derived by combining elements from other known maxi-K openers. However, 8a suffered from poor aqueous solubility, which complicated elucidation of SAR during in vitro evaluation. The activity of 8a in in vivo stroke models and studies directed toward improving its solubility are reported herein. Enhanced solubility was achieved by appending heterocycles to the 8a scaffold, and a notable observation was made that inclusion of a simple amino group (anilines 8k and 8l) yielded excellent in vitro maxi-K ion channel opening activity and enhanced brain-to-plasma partitioning compared to the appended heterocycles.
Triazole derivatives
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, (2011/03/17)
The present invention relates to triazole and imidazole derivatives of formula I and to their pharmaceutically acceptable acid addition salts. These compounds are NMDA receptor subtype blockers and are useful for the treatment of diseases related to the NMDA receptor.
