- Synthesis, Docking, and Biological activities of novel Metacetamol embedded [1,2,3]-triazole derivatives
-
ERα controls the breast tissue development and progression of breast cancer. In our search for novel compounds to target Estrogen Receptor Alpha Ligand-Binding Domain, we identified “N-(3-((1H-1,2,3-triazol-4-yl)methoxy)phenyl)acetamide” derivatives as lead compounds. The Docking studies indicated good docking score for Metacetamol derivatives when docked into the 1XP6. A series of metacetamol derivatives have been synthesized, characterized and evaluated for cytotoxicity, anti bacterial and anti oxidant activities. Among the tested twelve hybrid compounds, “7a, 7g, 7h and 7i” derivatives showed promising cytotoxicity with IC50 value of 50 value of 30 μM, whereas Compounds “7a, 7b, 7c, 7d, 7g, 7j, 7k and 7l” showed moderate anti bacterial activity with the MIC value of 300 μM.
- Battu, Satyanarayana,Joolakanti, Hima Bindhu,Kamepalli, Ramanjaneyulu,Miryala, Jeevanreddy
-
-
- An air-tolerant polymer gel-immobilized iridium photocatalyst with pumping recyclability properties
-
A novel methacrylate-based cross-linked polymer gel bearing an iridium photocatalyst showed air tolerance and pumping recyclability features through its tunable swelling and deswelling ability. The photocatalytic activity of the polymer gel was demonstrated through an E-to-Z isomerisation reaction and in an azide-alkene [2+3] cycloaddition.
- Abramov, Alex,Díaz Díaz, David,Maiti, Binoy,Reiser, Oliver
-
p. 7762 - 7765
(2021/08/13)
-
- One-Pot Deoxygenation and Substitution of Alcohols Mediated by Sulfuryl Fluoride
-
Sulfuryl fluoride is a valuable reagent for the one-pot activation and derivatization of aliphatic alcohols, but the highly reactive alkyl fluorosulfate intermediates limit both the types of reactions that can be accessed as well as the scope. Herein, we report the SO2F2-mediated alcohol substitution and deoxygenation method that relies on the conversion of fluorosulfates to alkyl halide intermediates. This strategy allows the expansion of SO2F2-mediated one-pot processes to include radical reactions, where the alkyl halides can also be exploited in the one-pot deoxygenation of primary alcohols under mild conditions (52-95% yield). This strategy can also enhance the scope of substitutions to nucleophiles that are previously incompatible with one-pot SO2F2-mediated alcohol activation and enables substitution of primary and secondary alcohols in 54-95% yield. Chiral secondary alcohols undergo a highly stereospecific (90-98% ee) double nucleophilic displacement with an overall retention of configuration.
- Epifanov, Maxim,Mo, Jia Yi,Dubois, Rudy,Yu, Hao,Sammis, Glenn M.
-
p. 3768 - 3777
(2021/03/01)
-
- [1,3]-Claisen rearrangement via removable functional group mediated radical stabilization
-
A thermal O-to-C [1,3]-rearrangement of α-hydroxy acid derived enol ethers was achieved under mild conditions. The 2-aminothiophenol protection of carboxylic acids facilitates formation of the [1,3] precursor and its thermal rearrangement via stabilization of a radical intermediate. Experimental and theoretical evidence for dissociative radical pair formation, its captodative stability via aminothiophenol, and a unique solvent effect are presented. The aminothiophenol was deprotected from rearrangement products as well as after derivatization to useful synthons.
- Alam, Md Nirshad,Dash, Soumya Ranjan,Mukherjee, Anirban,Pandole, Satish,Marelli, Udaya Kiran,Vanka, Kumar,Maity, Pradip
-
supporting information
p. 890 - 895
(2021/02/01)
-
- New 3-(1H-benzo[d]imidazol-2-yl)quinolin-2(1H)-one-based triazole derivatives: Design, synthesis, and biological evaluation as antiproliferative and apoptosis-inducing agents
-
A series of 1,2,3-triazole derivatives based on the quinoline–benzimidazole hybrid scaffold was designed, synthesized, and screened against a panel of NCI-60 humanoid cancer cell lines for in vitro cytotoxicity evaluation, which revealed that compound Q6 was the most potent cytotoxic agent with excellent GI50, TGI, and LC50 values on multiple cancer cell lines. Q6 was tested further on the BT-474 breast cancer line to evaluate the mechanism of action. Preliminary screening studies based on the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide assay revealed that compound Q6 had an excellent antiproliferative effect against human breast cancer cells, BT-474, with IC50 values of 0.59 ± 0.01 μM. The detailed study based on the acridine orange/ethidium bromide staining (AO/EB) and the 4′,6-diamidino-2-phenylindole (DAPI) assay suggested that the antiproliferative activity shown was due to the induction of apoptosis on exposure to Q6. Further, DCFDA staining showed the generation of reactive oxygen species, altering the mitochondrial potential and leading to the initiation of apoptosis. This was further supported by JC-1 staining, indicating that this scaffold can contribute to the development of more potent derivatives.
- Gaikwad, Nikhil B.,Bansode, Sapana,Biradar, Shankar,Ban, Mayuri,Srinivas, Nanduri,Godugu, Chandraiah,Yaddanapudi, Venkata M.
-
-
- Continuous photochemical benzylic bromination using: In situ generated Br2: Process intensification towards optimal PMI and throughput
-
The detailed development of photochemical benzylic brominations using a NaBrO3/HBr bromine generator in continuous flow mode is reported. Optimization of the bromine generator enables highly efficient mass utilization by HBr recycling, coupled with fast interphase transfer within a microstructured photochemical reactor (405 nm LEDs). Intensification of the reaction system, including complete removal of organic solvent, allowed a reduction in PMI from 13.25 to just 4.33. The photochemical transformation achieved exceptionally high throughput, providing complete conversion in residence times as low as 15 s. The organic solvent-free preparation of two pharmaceutically relevant building blocks was demonstrated with outstanding mass efficiency, by monobromination (1.17 kg scale in 230 min, PMI = 3.08) or dibromination (15 g scale in 20 min, PMI = 3.64).
- Steiner, Alexander,Williams, Jason D.,De Frutos, Oscar,Rincón, Juan A.,Mateos, Carlos,Kappe, C. Oliver
-
supporting information
p. 448 - 454
(2020/02/13)
-
- Design and synthesis of substituted (1-(benzyl)-1: H -1,2,3-triazol-4-yl)(piperazin-1-yl)methanone conjugates: Study on their apoptosis inducing ability and tubulin polymerization inhibition
-
A library of substituted (1-(benzyl)-1H-1,2,3-triazol-4-yl)(piperazin-1-yl)methanone derivatives were designed, synthesized and screened for their in vitro cytotoxic activity against BT-474, HeLa, MCF-7, NCI-H460 and HaCaT cells by employing 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Among all the synthesized analogues, compound 10ec displayed the highest cytotoxicity with the IC50 value of 0.99 ± 0.01 μM towards BT-474 cancer cell line. The target compound (10ec) was also evaluated for its tubulin polymerization inhibition study. Detailed biological studies such as acridine orange/ethidium bromide (AO/EB), DAPI and annexin V-FITC/propidium iodide staining assay suggested that compound 10ec induced the apoptosis of BT-474 cells. The clonogenic assay revealed that the inhibition of colony formation in BT-474 cells by 10ec in concentration-dependent manner. Moreover, the flow cytometric analysis revealed that 10ec induced apoptosis via cell cycle arrest at the sub-G1 and G2/M phase. In silico studies of sulfonyl piperazine-integrated triazole conjugates unveil that they possess drug-like properties. According to the molecular modelling studies, compound 10ec binds to the colchicine binding site of the tubulin.
- Alvala, Mallika,Babu, Bathini Nagendra,Devi, Ganthala Parimala,Godugu, Chandraiah,Manasa, Kesari Lakshmi,Nagesh, Narayana,Sigalapalli, Dilep Kumar,Thatikonda, Sowjanya,Vuppaladadium, Sowmya
-
supporting information
p. 1295 - 1302
(2020/12/01)
-
- Anti-oligomerization sheet molecules: Design, synthesis and evaluation of inhibitory activities against α-synuclein aggregation
-
Aggregation of α-synuclein (α-Syn) play a key role in the development of Parkinson Disease (PD). One of the effective approaches is to stabilize the native, monomeric protein with suitable molecule ligands. We have designed and synthesized a series of sheet-like conjugated compounds which possess different skeletons and various heteroatoms in the two blocks located at both ends of linker, which have good π-electron delocalization and high ability of hydrogen-bond formation. They have shown anti-aggregation activities in vitro towards α-Syn with IC50 down to 1.09 μM. The molecule is found binding in parallel to the NACore within NAC domain of α-Syn, interfering aggregation of NAC region within different α-Syn monomer, and further inhibiting or slowing down the formation of α-Syn oligomer nuclei at lag phase. The potential inhibitor obtained by our strategy is considered to be highly efficient to inhibit α-Syn aggregation.
- Liu, Hao,Chen, Li,Zhou, Fei,Zhang, Yun-Xiao,Xu, Ji,Xu, Meng,Bai, Su-Ping
-
supporting information
p. 3089 - 3096
(2019/06/14)
-
- Synthesis and biological evaluation of 1-benzyl-N-(2-(phenylamino)pyridin-3-yl)-1H-1,2,3-triazole-4-carboxamides as antimitotic agents
-
A library of 1-benzyl-N-(2-(phenylamino)pyridin-3-yl)-1H-1,2,3-triazole-4-carboxamides (7a–al) have been designed, synthesized and screened for their anti-proliferative activity against some selected human cancer cell lines namely DU-145, A-549, MCF-7 and HeLa. Most of them have shown promising cytotoxicity against lung cancer cell line (A549), amongst them 7f was found to be the most potent anti-proliferative congener. Furthermore, 7f exhibited comparable tubulin polymerization inhibition (IC50 value 2.04 μM) to the standard E7010 (IC50 value 2.15 μM). Moreover, flow cytometric analysis revealed that this compound induced apoptosis via cell cycle arrest at G2/M phase in A549 cells. Induction of apoptosis was further observed by examining the mitochondrial membrane potential and was also confirmed by Hoechst staining as well as Annexin V-FITC assays. Furthermore, molecular docking studies indicated that compound 7f binds to the colchicine binding site of the β-tubulin. Thus, 7f exhibits anti-proliferative properties by inhibiting the tubulin polymerization through the binding at the colchicine active site and by induction of apoptosis.
- Prasad, Budaganaboyina,Lakshma Nayak,Srikanth,Baig, Mirza Feroz,Subba Reddy,Babu, Korrapati Suresh,Kamal, Ahmed
-
p. 535 - 548
(2018/11/26)
-
- Synthesis process for empagliflozin
-
The invention relates to a synthesis process for empagliflozin. The synthesis process for empagliflozin comprises the following steps: taking 4-fluorotoluene as a starting material; carrying out radical bromo reaction, Friedel-Crafts alkylation reaction, deprotection, diazotization chlorination and alkylation reaction to obtain an intermediate which is (S)-3-(4-(5-bromo-2-chlorobenzyl) phenoxyl) tetrahydrofuran; and then carrying out condensation, etherification and methoxyl removal on the intermediate and 2,3,4,6-quadri-O-trimethylsilyl-D-glucolactone to obtain the empagliflozin as a hypoglycemic drug. The synthesis process for empagliflozin has the advantages that compared with an existing synthesis process, the synthesis process for the empagliflozin takes the 4-fluorotoluene as the starting material, raw materials are cheap and easy to obtain, industrialization is easy to implement in the process, the synthesis route is short, and the process is easy to operate; in a preparation process, various temperature conditions are easy to control, reaction conversion rate is high, and the total yield can be 70% or above; and moreover, by the synthesis process, the product cannot be isomerized easily, impurities are fewer, the purity of the product can be improved, and the purity can be 99% or above.
- -
-
Paragraph 0016
(2018/03/28)
-
- Light Harvesting for Rapid and Selective Reactions: Click Chemistry with Strain-Loadable Alkenes
-
Intramolecular strain is a powerful driving force for rapid and selective chemical reactions, and it is the cornerstone of strain-induced bioconjugation. However, the use of molecules with built-in strain is often complicated as a result of instability or selectivity issues. Here, we show that such strain, and subsequent cycloadditions, can be mediated by visible light via the harvesting of photochemical energy. Through theoretical investigations and molecular engineering of strain-loadable cycloalkenes, we demonstrate the rapid chemoselective cycloaddition of alkyl azides with unstrained cycloalkenes via the transiently (reversibly) formed trans-cycloalkene. We assess this system via the rapid bioconjugation of azide-functionalized insulin. An attractive feature of this process is the cleavable nature of the linker, which makes a catch-and-release strategy possible. In broader terms, we show that conversion of photochemical energy to intramolecular ring strain is a powerful strategy that can facilitate complex chemical transformations, even in biomolecular systems. Probing, isolating, and/or manipulating biologically relevant macromolecules is central to the study of their function in living systems. However, the synthetic tools available for performing the chemistry necessary for such studies are often difficult to use or limited in utility. In the approach presented here, light is converted to molecular strain energy, which can in turn be used for performing rapid and highly selective chemistry on macromolecular systems. Because it involves chemically stable and chemoselective reactions, this research not only opens up new possibilities for biomolecular functionalization and manipulation but also promises to make such experiments accessible to a broader class of researchers. The central concept of strain-loadable alkenes is general and provides a firm foundation for light-activated chemistry in complex environments. Strain-loadable alkenes are cycloalkenes that, when irradiated in the presence of a visible-light-absorbing photocatalyst, undergo double-bond isomerization. Because of engineered geometrical constraints, this isomerization results in significant molecular strain. Weaver and colleagues exploit this strain to dramatically accelerate the cycloaddition with azides, which are otherwise unreactive, in mixed molecular environments.
- Singh, Kamaljeet,Fennell, Christopher J.,Coutsias, Evangelos A.,Latifi, Reza,Hartson, Steve,Weaver, Jimmie D.
-
p. 124 - 137
(2018/01/17)
-
- Synthesis and biological evaluation of curcumin inspired indole analogues as tubulin polymerization inhibitors
-
In our endeavour towards the development of potent cytotoxic agents, a series of some new curcumin inspired indole analogues, in which indole and phenyl moieties are linked on either sides of 1,5-diaryl-1,4-pentadien-3-one system have been synthesized and characterized by spectral data. All the newly synthesized analogues were tested for their cytotoxic potential against a panel of eight cancer cell lines namely, lung (A549), breast (MDA-MB-231, BT549 and 4T1), prostate (PC-3, DU145), gastric (HGC-27) and cervical (HeLa). Notably, among all the compounds tested, compounds 11c, 11d and 11f showed potent growth inhibition on PC-3 and BT549 with IC50values in the range of 3.12–6.34?μM and 4.69–8.72?μM respectively. The most active compound (11c) was also tested on RWPE-1 (normal prostate) cells and was found to be safe compared to the PC-3?cells. In tubulin polymerization assay, compounds 11c and 11f effectively inhibited microtubule assembly with IC50values of 10.21?±?0.10 and 8.83?±?0.06?μM respectively. The results from molecular modelling studies revealed that these compounds bind at the colchicine binding site of the tubulin. Moreover, DAPI and acridine orange/ethidium bromide staining studies indicated that compounds 11c and 11f can induce apoptosis in PC-3?cells. Further flow-cytometry analysis revealed that compound 11c arrests PC-3?cells in G2/M phase of the cell cycle while compound 11f treatment resulted in moderate increase in the G2/M population. Additionally, the treatment by these compounds led to the impairment of mitochondrial membrane potential (DΨm) in PC-3?cells.
- Sri Ramya,Angapelly, Srinivas,Guntuku, Lalita,Singh Digwal, Chander,Nagendra Babu, Bathini,Naidu,Kamal, Ahmed
-
p. 100 - 114
(2016/12/30)
-
- Design and synthesis of imidazo[2,1-b]thiazole linked triazole conjugates: Microtubule-destabilizing agents
-
A series of imidazo[2,1-b]thiazole linked triazole conjugates were synthesized by using Huisgen 1,3-dipolar cyclo-addition reaction (click chemistry approach) and evaluated for their antiproliferative activity against some human cancer cell lines like, HeLa (cervical), DU-145 (prostate), A549 (lung), MCF-7 (breast) and HepG2 (liver). Among them, Conjugates 4g and 4h demonstrated a significant antiproliferative effect against human lung cancer cells (A549) with IC50values of 0.92 and 0.78 μM respectively. Flow cytometric analysis revealed that these conjugates induced cell cycle arrest in G2/M phase in A549 lung cancer cells. The tubulin polymerization assay and immunofluorescence analysis showed that these conjugates effectively inhibit microtubule assembly in cell free and cell based (A549) experiment respectively. Moreover, the apoptosis inducing properties were evaluated by Hoechst staining, mitochondrial membrane potential and Annexin V-FITC assay. Further, western blot analysis was performed for proapoptotic protein Bax and antiapoptotic protein Bcl-2 and the results demonstrated that there was up regulation of Bax and down regulation of Bcl-2 suggesting that these compounds induced apoptosis in human lung cancer cells, A549.
- Shaik, Siddiq Pasha,Nayak, V. Lakshma,Sultana, Faria,Rao, A.V. Subba,Shaik, Anver Basha,Babu, Korrapati Suresh,Kamal, Ahmed
-
-
- Design and synthesis of 1,2,3-triazolo linked benzo[d]imidazo[2,1-b]thiazole conjugates as tubulin polymerization inhibitors
-
1,2,3-Triazolo linked benzo[d]imidazo[2,1-b]thiazole conjugates (5a–v) were designed, synthesized and evaluated for their cytotoxic potency against some human cancer cell lines like DU-145 (prostate), HeLa (cervical), MCF-7 (breast) HepG2 (liver) and A549 (lung). Preliminary results revealed that some of these conjugates like 5f and 5k exhibited significant antiproliferative effect against human breast cancer cells (MCF-7) with IC50 values of 0.60 and 0.78?μM respectively. Flow cytometric analysis of the cell cycle demonstrated an increase in the percentage of cells in the G2/M phase which was further authenticated by elevation of cyclin B1 protein levels. Immunocytochemistry revealed loss of intact microtubule structure in cells treated with 5f and 5k, and western blot analysis revealed that these conjugates accumulated more tubulin in the soluble fraction. Moreover, the conjugates caused apoptosis of the cells that was confirmed by mitochondrial membrane potential and Annexin V-FITC assay. Molecular docking studies indicated that these conjugates occupy the colchicine binding site of the tubulin protein.
- Shaik, Siddiq Pasha,Vishnuvardhan,Sultana, Faria,Subba Rao,Bagul, Chandrakant,Bhattacharjee, Debanjan,Kapure, Jeevak Sopanrao,Jain, Nishant,Kamal, Ahmed
-
p. 3285 - 3297
(2017/05/29)
-
- Synthesis of Novel Triazole-incorporated Isatin Derivatives as Antifungal, Antitubercular, and Antioxidant Agents and Molecular Docking Study
-
A library of 1,2,3-triazoles efficiently prepared via click chemistry and evaluated for their antifungal, antitubercular, antioxidant, cytotoxicity, molecular docking and ADME prediction.
- Shaikh, Mubarak H.,Subhedar, Dnyaneshwar D.,Khan, Firoz A. Kalam,Sangshetti, Jaiprakash N.,Nawale, Laxman,Arkile, Manisha,Sarkar, Dhiman,Shingate, Bapurao B.
-
supporting information
p. 413 - 421
(2017/02/03)
-
- Synthesis, in Vitro Evaluation, and Radiolabeling of Fluorinated Puromycin Analogues: Potential Candidates for PET Imaging of Protein Synthesis
-
There is currently no ideal radiotracer for imaging of protein synthesis rate (PSR) by positron emission tomography (PET). Existing fluorine-18-labeled amino acid-based radiotracers predominantly visualize amino acid transporter processes, and in many cases they are not incorporated into nascent proteins at all. Others are radiolabeled with the short-half-life positron emitter carbon-11, which is rather impractical for many PET centers. Based on the puromycin (6) structural manifold, a series of 10 novel derivatives of 6 was prepared via Williamson ether synthesis from a common intermediate. A bioluminescence assay was employed to study their inhibitory action on protein synthesis, which identified the fluoroethyl analogue 7b as a lead compound. The fluorine-18 analogue was prepared via nucleophilic substitution of the corresponding tosylate precursor in a modest radiochemical yield of 2 ± 0.6% with excellent radiochemical purity (>99%) and showed complete stability over 3 h at ambient temperature.
- Betts, Helen M.,Milicevic Sephton, Selena,Tong, Carmen,Awais, Ramla O.,Hill, Philip J.,Perkins, Alan C.,Aigbirhio, Franklin I.
-
supporting information
p. 9422 - 9430
(2016/11/11)
-
- Synthesis and bioactivity of novel triazole incorporated benzothiazinone derivatives as antitubercular and antioxidant agent
-
In search of new active molecules against Mycobacterium tuberculosis (MTB) H37Ra and M. bovis BCG, a small focused library of benzothiazinone based 1,2,3-triazoles has been efficiently prepared via click chemistry approach. Several derivatives were found to be promising inhibitors of MTB and M. bovis BCG characterized by lower MIC values (27.34-29.37 μg/mL). Among all the synthesized compounds, 6c and 6e is the most active compound against MTB and M. bovis BCG. The compounds were further tested for anti-proliferative activity against HeLa, A549 and A431 cell lines using MTT assay and showed no significant cytotoxic activity at the maximum concentration evaluated. Further, the synthesized compounds were found to have potential antioxidant activity with IC50 range = 14.14-47.11 μg/mL. Furthermore, to rationalize the observed biological activity data, the molecular docking study also been carried out against a potential target MTB DprE1, which revealed a significant correlation between the binding score and biological activity for these compounds. The results of the in vitro and in silico study suggest that the triazole incorporated benzothiazinone may possess the ideal structural requirements for further development of novel therapeutic agents.
- Shaikh, Mubarak H.,Subhedar, Dnyaneshwar D.,Arkile, Manisha,Khedkar, Vijay M.,Jadhav, Nandadeep,Sarkar, Dhiman,Shingate, Bapurao B.
-
p. 561 - 569
(2016/01/09)
-
- Synthesis and Biological Evaluation of 1,2,3-triazole tethered Pyrazoline and Chalcone Derivatives
-
A series of pyrazoline derivatives and corresponding chalcone intermediates with substituents same as combretastatin-A4(CA-4) conjugated with triazole nucleus has been synthesized and evaluated for their anticancer potential. Sulphorhodamine B(SRB) assay indicated compound 12c to be the most active compound from the series with GI50 value of 6.7 μm against the human liver carcinoma cell line HepG2. Interestingly, the intermediate 11c exhibited more promising cytotoxicity demonstrating GI50 value of 1.3 μm against the prostate cancer cell line DU145. Compounds 11c and 12c caused accumulation of cells in G2/M phase and inhibited tubulin polymerization. Furthermore, these compounds reduce the mitochondrial membrane potential and activate caspases 3 and 9, thereby indicating their ability to trigger apoptosis.
- Hussaini, Syed Mohammed Ali,Yedla, Poornachandra,Babu, Korrapati Suresh,Shaik, Thokhir B.,Chityal, Ganesh Kumar,Kamal, Ahmed
-
-
- Discovery and structural optimization of 4-(4-(benzyloxy)phenyl)-3,4-dihydropyrimidin-2(1H)-ones as RORc inverse agonists
-
Aim: Retinoic acid receptor-related orphan nuclear receptors (RORs) are orphan nuclear receptors that show constitutive activity in the absence of ligands. Among 3 subtypes of RORs, RORc is a promising therapeutic target for the treatment of Th17-mediated autoimmune diseases. Here, we report novel RORc inverse agonists discovered through structure-based drug design. Methods: Based on the structure of compound 8, a previously described agonist of RORa, a series of 4-(4-(benzyloxy)phenyl)-3,4-dihydropyrimidin-2(1H)-one derivatives were designed and synthesized. The interaction between the compounds and RORc was detected at molecular level using AlphaScreen assay. The compounds were further examined in 293T cells transfected with RORc and luciferase reporter gene. Thermal stability shift assay was used to evaluate the effects of the compounds on protein stability. Results: A total of 27 derivatives were designed and synthesized. Among them, the compound 22b was identified as the most potent RORc inverse agonist. Its IC50 values were 2.39 μmol/L in AlphaScreen assay, and 0.82 μmol/L in inhibition of the cell-based luciferase reporter activity. Furthermore, the compound 22b displayed a 120-fold selectivity for RORc over other nuclear receptors. Moreover, a molecular docking study showed that the structure-activity relationship was consistent with the binding mode of compound 22b in RORc. Conclusion: 4-(4-(Benzyloxy)phenyl)-3,4-dihydropyrimidin-2(1H)-one derivatives are promising candidates for the treatment of Th17-mediated autoimmune diseases, such as rheumatoid arthritis, psoriasis, and multiple sclerosis.
- Wu, Xi-Shan,Wang, Rui,Xing, Yan-Li,Xue, Xiao-Qian,Zhang, Yan,Lu, Yong-Zhi,Song, Yu,Luo, Xiao-Yu,Wu, Chun,Zhou, Yu-Lai,Jiang, Jian-Qin,Xu, Yong
-
p. 1516 - 1524
(2016/11/11)
-
- 1,2,3-Triazole incorporated coumarin derivatives as potential antifungal and antioxidant agents
-
A series of novel ethyl-7-((1-(benzyl)-1H-1,2,3-triazol-4-yl)methoxy)-2-oxo-2H-chromene-3-carboxylates 8a-h as potential antifungal agents were synthesized via click chemistry. The antifungal activity was evaluated against five human pathogenic fungal strains, such as Candida albicans, Fusarium oxysporum, Aspergillus flavus, Aspergillus niger and Cryptococcus neoformans. Compound 8c, 8d, 8e and 8h were found to be equipotent against C. albicans when compared with miconazole and compound 8f was found to be two-fold more active compared with miconazole and equipotent to fluconazole against C. albicans. The coumarin-based triazole derivatives were also evaluated for antioxidant activity and compound 8a was found to be potent antioxidant when compared with standard drug. Furthermore, molecular docking study of the newly synthesized compounds was performed and results showed good binding mode in the active site of fungal C. albicans enzyme P450 cytochrome lanosterol 14α-demethylase. Moreover, the synthesized compounds were also analyzed for ADME properties and showed potential to build up as good oral drug candidates.
- Shaikh, Mubarak H.,Subhedar, Dnyaneshwar D.,Khan, Firoz A. Kalam,Sangshetti, Jaiprakash N.,Shingate, Bapurao B.
-
p. 295 - 301
(2018/03/22)
-
- Direct halogenation of alcohols with halosilanes under catalyst- and organic solvent-free reaction conditions
-
A chemoselective method for the direct halogenation of different types of alcohols with halosilanes under catalyst- and solvent-free reaction conditions (SFRC) is reported. Various primary, secondary and tertiary benzyl alcohols and tertiary alkyl alcohols were directly transformed to the corresponding benzyl and alkyl halides, respectively, using chlorotrimethylsilane (TMSCl) and bromotrimethylsilane (TMSBr).
- Ajvazi, Njomza,Stavber, Stojan
-
supporting information
p. 2430 - 2433
(2016/05/19)
-
- One-Step Synthesis of Substituted Benzofurans from ortho- Alkenylphenols via Palladium-Catalyzed C=H Functionalization
-
A dehydrogenative oxygenation of C(sp2)=H bonds with intramolecular phenolic hydroxy groups has been developed, which provides a straightforward and concise access to structurally diversely benzofurans from ortho-alkenylphenols. The reaction is catalyzed by palladium on carbon (Pd/C) without any oxidants and sacrificing hydrogen acceptors.
- Yang, Dejun,Zhu, Yifei,Yang, Na,Jiang, Qiangqiang,Liu, Renhua
-
supporting information
p. 1731 - 1735
(2016/06/09)
-
- Synthesis of 2-anilinopyridyl-triazole conjugates as antimitotic agents
-
A series of 2-anilinopyridyl-triazole conjugates (6a-t) were prepared and evaluated for their cytotoxic activity against a panel of three human cancer cell lines. Among them compounds 6q, 6r and 6s showed significant cytotoxic activity with IC50 values ranging from 0.1 to 4.1 μM. Structure-activity relationships were elucidated with various substitutions on these conjugates. Flow cytometric analysis revealed that these compounds arrest the cell cycle at the G2/M phase and induce cell death by apoptosis. The tubulin polymerization assay and immunofluorescence analysis showed that these compounds (6q, 6r and 6s) effectively inhibited the microtubule assembly in human prostate cancer cells (DU-145). The docking studies showed that 6s interacts and binds efficiently with the tubulin protein at the colchicine binding site. This was further confirmed by the colchicine competitive binding assay. Moreover, compounds 6q, 6r and 6s possess anti-tubulin activity both in vitro and within cells as demonstrated by the ratio of soluble versus polymerized tubulin. Further the apoptotic effects of compounds were confirmed by Hoechst staining, caspase 3 activation, annexin-V FITC, mitochondrial membrane potential and DNA fragmentation analysis. Interestingly, these compounds did not affect the normal human embryonic kidney cells, HEK-293.
- Kamal, Ahmed,Subba Rao,Vishnuvardhan,Srinivas Reddy,Swapna, Konderu,Bagul, Chandrakant,Subba Reddy,Srinivasulu, Vunnam
-
p. 4879 - 4895
(2015/05/05)
-
- Synthesis and biological evaluation of pyrazolo-triazole hybrids as cytotoxic and apoptosis inducing agents
-
A series of pyrazolo-triazole hybrids were designed and synthesized by combining the 1,3-diphenyl pyrazole and triazole scaffolds to obtain (1-benzyl-1H-1,2,3-triazol-4-yl)(1,3-diphenyl-1H-pyrazol-4-yl)methanones. All the synthesized compounds were screened for their anticancer activity against four tumor cell lines, viz. HT-29 (colon), PC-3 (prostate), A549 (lung), and U87MG (glioblastoma) cells. Most of the tested compounds showed moderate to potent cell growth inhibition on different cancer cells, in particular, the compounds 17, 23, and 29 exhibited promising cytotoxicity against these cell lines with the IC50 values in the range of 0.86-3.72 μM. In addition, the potential mechanism of cell growth inhibition and apoptotic induction by these compounds was investigated in U87MG cancer cells using cell-based assays, including wound healing assay, flow cytometry, Hoechst staining, acridine orange/ethidium bromide staining, Annexin V-FITC/propidium Iodide dual staining, Rhodamine 123 staining, and carboxy-DCFDA staining. The results indicate that the compounds induce apoptosis in U87MG cells via mitochondrial pathway through up-regulation of pro-apoptotic (Bax) and down-regulation of anti-apoptotic (Bcl-2) genes. Based on these studies, three compounds 17, 23 and 29 have been identified as promising new molecules that have the potential to be developed as leads.
- Srinivasa Reddy,Kulhari, Hitesh,Ganga Reddy,Subba Rao,Bansal, Vipul,Kamal, Ahmed,Shukla, Ravi
-
p. 10136 - 10149
(2015/10/20)
-
- Generation of α-imino gold carbenes through gold-catalyzed intermolecular reaction of azides with ynamides
-
The generation of α-imino gold carbenes via gold-catalyzed intermolecular reaction of azides and ynamides is disclosed. This new methodology allows for highly regioselective access to valuable 2-aminoindoles and 3-amino-β-carbolines in generally good to excellent yields. A mechanistic rationale for this tandem reaction, especially for the observed high regioselectivity, is supported by DFT calculations.
- Shu, Chao,Wang, Yong-Heng,Zhou, Bo,Li, Xin-Ling,Ping, Yi-Fan,Lu, Xin,Ye, Long-Wu
-
supporting information
p. 9567 - 9570
(2015/08/18)
-
- Palladium(0)-catalyzed cyclopropanation of benzyl bromides via C(sp 3)-H bond activation
-
A novel and highly efficient Pd(0)-catalyzed domino reaction to prepare cyclopropane derivatives has been established. The process involves a Heck-type coupling reaction and a C(sp3)-H bond activation. Preliminary DFT calculations suggest that a four-membered palladacycle intermediate is involved. This journal is the Partner Organisations 2014.
- Mao, Jiangang,Zhang, Shuo-Qing,Shi, Bing-Feng,Bao, Weiliang
-
p. 3692 - 3694
(2014/04/03)
-
- CuI-catalyzed coupling of gem-dibromovinylanilides and sulfonamides: An efficient method for the synthesis of 2-amidoindoles and indolo[1,2-a] quinazolines
-
A Cu(I)-catalyzed, intermolecular protocol for the synthesis of 2-amidoindoles and tetrahydroindolo[1,2-a]quinazolines in shorter time and high yields is reported. The key highlight of this disclosure is the formation of 2-amidoindole and tetrahydroindolo[1,2-a]quinazoline moieties directly from gem-dibromovinylanilides and sulfonamides in a one-pot fashion through the in situ formation of ynamides followed by a base-promoted intramolecular hydroamidation.
- Kiruthika, Selvarangam E.,Perumal, Paramasivan Thirumalai
-
p. 484 - 487
(2014/04/03)
-
- Synthesis and evaluation of N-((1-benzyl-1H-1,2,3-triazol-4-yl)methyl) nicotinamides as potential anticancer agents that inhibit tubulin polymerization
-
A series of N-((1-benzyl-1H-1,2,3-triazol-4-yl)methyl)nicotinamides (4) was synthesized and tested for their anticancer activity against a panel of 60 human cancer cell lines. Some of the representative compounds such as 4a, 4b, 4f, 4g, 4i and 4t were selected for the five dose study and amongst them 4g and 4i displayed significant anticancer activity with GI50 values ranging from 0.25 to 8.34 and 1.42 to 5.86 μM, respectively. Cell cycle analysis revealed that these compounds induced cell cycle arrest at G2/M phase in MCF-7 cells. The most active compound in this series 4g also inhibited tubulin polymerization with IC50 value 1.93 μM superior to that of E7010. Moreover, assay to investigate the effect on caspase-9, Hoechst staining and DNA fragmentation analysis suggested that these compounds induced cell death by apoptosis. Docking experiments showed that they interact and bind efficiently with tubulin protein. Overall, the results demonstrate that N-((1-benzyl-1H-1,2, 3-triazol-4-yl)methyl)nicotinamide scaffold possess anticancer property by inhibiting the tubulin polymerization.
- Kamal, Ahmed,Reddy, N.V. Subba,Nayak, V. Lakshma,Bolla, Narasimha Rao,Subba Rao,Prasad
-
p. 3465 - 3477
(2014/06/23)
-
- Revisiting the bromination of c-h bonds with molecular bromine by using a photo-microflow system
-
The photobromination of C-H bonds by using molecular bromine was reinvestigated under microfluidic conditions. The continuous-flow method suppressed the production of dibrominated compounds and effectively produced the desired monobrominated products with high selectivity. Rapid bromination of benzylic substrates containing a photoaffinity azide group was achieved without any decomposition. Go with the (micro)flow: Photobromination of C-H bonds by using molecular bromine under microfluidic conditions has been investigated (see scheme). The continuous-flow method suppressed the production of dibrominated compounds and effectively produced the desired monobrominated compounds with high selectivity. Rapid bromination of benzylic substrates containing a photoaffinity azide group was achieved without any decomposition.
- Manabe, Yoshiyuki,Kitawaki, Yuriko,Nagasaki, Masahiro,Fukase, Koichi,Matsubara, Hiroshi,Hino, Yoshiko,Fukuyama, Takahide,Ryu, Ilhyong
-
supporting information
p. 12750 - 12753
(2015/03/30)
-
- Synthesis of combretastatin A4 analogues on steroidal framework and their anti-breast cancer activity
-
Combretastatin A4 analogues were synthesized on steroidal framework from gallic acid with a possibility of anti-breast cancer agents. Twenty two analogues were synthesized and evaluated for cytotoxicity against human breast cancer cell lines (MCF-7 & MDA-MB 231). The best analogue 22 showed potent antitubulin effect. Docking experiments also supported strong binding affinity of 22 to microtubule polymerase. In cell cycle analysis, 22 induced apoptosis in MCF-7 cells significantly. It was found to be non-toxic up to 300 mg/kg dose in Swiss albino mice in acute oral toxicity. This article is part of a Special Issue entitled "Synthesis and biological testing of steroid derivatives as inhibitors".
- Parihar, Swati,Kumar, Amit,Chaturvedi, Amit K.,Sachan, Naresh Kumar,Luqman, Suaib,Changkija, Bendangla,Manohar, Murli,Prakash, Om,Chanda,Khan, Feroz,Chanotiya,Shanker, Karuna,Dwivedi, Anila,Konwar, Rituraj,Negi, Arvind S.
-
p. 332 - 344
(2013/11/19)
-
- Fluorination of aryl boronic acids using acetyl hypofluorite made directly from diluted fluorine
-
Aryl boronic acids or pinacol esters containing EDG were converted in good yields and fast reactions to the corresponding aryl fluorides using the readily obtainable solutions of AcOF. In reactions with aryl boronic acids containing EWG at the para position, there are two competing forces: one directing the fluorination to take place ortho to the boronic acid and the other, toward an ipso substitution. With EWG meta to the boronic acid, substitution ipso to the boron moiety takes place in good yields.
- Vints, Inna,Gatenyo, Julia,Rozen, Shlomo
-
p. 11794 - 11797
(2014/01/06)
-
- Polyvinylpyrrolidone-bromine complex: An efficient polymeric reagent for selective preparation of benzyl bromides in the presence of hexamethyldisilane
-
Benzylic bromides were conveniently obtained in high yields via the reaction of the corresponding alcohols with crosslinked polyvinylpyrrolidone- bromine complex (PVPP-Br2)/hexamethyldisilane in chloroform at reflux condition. Selective conversion of benzyl alcohol to benzyl bromide in the presence of primary aliphatic alcohols, e.g. 2-phenylethanol was also achieved.
- Mokhtary, Masoud,Lakouraj, Moslem M.
-
p. 305 - 309
(2012/10/29)
-
- Microwave-assisted benzyl mono- and dibromination in diethyl carbonate as environmentally friendly alternative to radical bromination in carbon tetrachloride
-
An environmentally friendly benzyl mono- and di-bromination synthetic procedure was developed that is superior to the classic carbon tetrachloride bromination procedure in both reaction time and isolated yield. This new reaction was performed in diethyl carbonate as reaction media using microwave instead of conventional heating. Both the solvent and the brominating reagent N-bromosuccinimide (prepared from succinimide obtained from the reaction mixture) are recyclable. Practically, the preparation of our target compounds was completed in less than two hours. The Royal Society of Chemistry.
- Pingali, Subramanya R. K.,Upadhyay, Sunil K.,Jursic, Branko S
-
experimental part
p. 928 - 933
(2011/05/15)
-
- Benzylic bromination of toluene derivatives with boron tribromide
-
A facile method for the benzylic bromination of toluene derivatives was developed. Various substituted toluenes were brominated with boron tribromide as bromine source in carbon tetrachloride at room temperature, affording their corresponding benzyl bromides in good yields.
- Chen, Hongbiao,Shen, Litao,Lin, Yuanbin
-
experimental part
p. 998 - 1003
(2010/05/18)
-
- Visible-light-promoted Wohl-Ziegler functionalization of organic molecules with N-bromosuccinimide under solvent-free reaction conditions
-
The visible-light-induced transformation of toluenes with N-bromosuccinimide (NBS) under solvent-free reaction conditions (SFRC) was studied. The reaction took place in spite of the very restricted molecular motion; toluenes could be regioselectively converted to benzyl bromides. Selective radical-chain reactions with NBS were carried out in liquid/liquid and in solid/solid systems; furthermore, reactions could be performed in the presence of air. The radical scavenger TEMPO (=2,2,6,6-tetramethylpiperidin-1- yloxy) completely suppressed the side-chain bromination of toluenes with NBS under SFRC. Electron-withdrawing groups decreased the reactivity of the toluenes, and the Hammett reaction constant ρ+ = -1.7 indicated involvement of polar radical intermediates with electrophilic character.
- Jereb, Marjan,Zupan, Marko,Stavber, Stojan
-
scheme or table
p. 555 - 566
(2009/09/06)
-
- Highly efficient fluorine-promoted intramolecular condensation of benzo[c]phenanthrene: A new prospective on direct fullerene synthesis
-
Various functional groups have been tested as alternative promoters of the intramolecular condensation of benzo-[c]phenanthrene under flash vacuum pyrolysis conditions. Methyl and fluorine functionalization were found to be promising approaches. Unexpectedly high selectivity was observed in the cyclization of fluorinated benzo[c]phenanthrenes. The mechanism for the condensation reaction and the advantages of fluorine as a promoter for the rational synthesis of fullerenes are discussed. Wiley-VCH Verlag GmbH & Co. KGaA.
- Amsharov, Konstantin Yu.,Kabdulov, Mikhail A.,Jansen, Martin
-
experimental part
p. 6328 - 6335
(2011/03/19)
-
- Synthesis and in vitro affinities of various MDL 100907 derivatives as potential 18F-radioligands for 5-HT2A receptor imaging with PET
-
Radiolabelled piperidine derivatives such as [11C]MDL 100907 and [18F]altanserin have played an important role in diagnosing malfunction in the serotonergic neurotransmission. A variety of novel piperidine MDL 100907 derivatives, possible to label with 18F-fluorine, were synthesized to improve molecular imaging properties of [11C]MDL 100907. Their in vitro affinities to a broad spectrum of neuroreceptors and their lipophilicities were determined and compared to the clinically used reference compounds MDL 100907 and altanserin. The novel compounds MA-1 (53) and (R)-MH.MZ (56) show Ki-values in the nanomolar range towards the 5-HT2A receptor and insignificant binding to other 5-HT receptor subtypes or receptors. Interestingly, compounds MA-1 (53), MH.MZ (55) and (R)-MH.MZ (56) provide a receptor selectivity profile similar to MDL 100907. These compounds could possibly be preferable antagonistic 18F-tracers for visualization of the 5-HT2A receptor status. Medium affine compounds (VK-1 (32), (51), (52), (54)) were synthesized and have Ki values between 30 and 120 nM. All promising compounds show log P values between 2 and 3, that is, within the range of those for the established radiotracers altanserin and MDL 100907. The novel compounds MA-1 (53) and (R)-MH.MZ (56) thus appear to be promising high affine and selective tracers of 18F-labelled analogues for 5-HT2A imaging with PET.
- Herth, Matthias M.,Kramer, Vasko,Piel, Markus,Palner, Mikael,Riss, Patrick J.,Knudsen, Gitte M.,Roesch, Frank
-
experimental part
p. 2989 - 3002
(2009/09/05)
-
- FUSED PYRROLE COMPOUNDS, PHARMACEUTICAL AGENTS CONTAINING THE SAME, AND THE USE THEREOF
-
The present invention relates to fused pyrrole compounds of the formula 1. in which at least one of the radicals R1, R2, R3 is 4-sulphur-substituted phenyl. These compounds are in particular pyrrolizines, indolizines and heteroanalogues having selective inhibitory action on isoenzyme-2 of prostaglandin H synthase (COX-2). The invention also relates to pharmaceutical compositions which contain these compounds; and the use of these compounds for the treatment of disorders of the rheumatic type.
- -
-
-
- [4,5]-fused-3,6-disubstituted-pyridazines with sulfur-containing substituents in position three for the treatment of neoplasia
-
[4,5]-Fused-3,6 disubstituted-pydidazines of Formula I are useful for inducing or promoting apoptosis and for arresting uncontrolled neoplastic cell proliferation, and are specifically useful in the arresting and treatment of neoplasia: wherein Y1and Y2are independently selected from the group consisting of (CH2)n,—C(X)—NH—,—(CH2)n—C(X)—O—, and X is O or S; R1is selected from the group consisting of lower alkyl, lower alkenyl, lower alkynyl, and substituted or unsubstituted phenyl, pyridinyl, and the like; R2is selected from the group consisting of substituted or unsubstituted phenyl, benzyl, pyridinyl, and the like; “A” is a benzene ring fused with the pyridazine ring; and R3is independently selected in each instance form the group consisting of halogen, lower alkyl, and the like.
- -
-
-
- HETEROCYCLIC INDOLE DERIVATIVES AND MONO- OR DIAZAINDOLE DERIVATIVES
-
Indole derivatives and mono- or diazaindole derivatives represented by general formula (1), pharmaceutically acceptable acid-addition salts or base-addition salts thereof or hydrates of the same which have a COX-2 inhibitory activity and are useful as drugs such as anti-inflammatory agents, wherein Het represents an optionally substituted heterocycle; A1 and A2 independently represent each -CH=, etc.; A3 represents -CH2-, etc.; R1 represents 4-fluorophenyl, etc.; R2 represents alkyl; and n is 0, 1 or 2, provided that when A1 and A2 are both -CH=, then A3 is -CH2- or -SO2-.
- -
-
-
- Reductive bromination of aromatic aldehydes using alkylboron dibromides
-
The reductive bromination of aromatic aldehydes with isopinocampheyl boron dibromide in hexane at room temperature produces the corresponding benzyl bromides in excellent yields. (C) 2000 Elsevier Science Ltd.
- Kabalka, George W.,Wu, Zhongzhi,Ju, Yuhong
-
p. 5161 - 5164
(2007/10/03)
-
- Thermodynamic Stabilities of Phenonium Ions Based on Bromide-Transfer Equilibria in the Gas Phase
-
The thermodynamic stabilities of the phenonium (ethylenebenzenium) ion and ring-substituted derivatives were determined based on the bromide-transfer equilibria in the gas phase. It has been shown that the phenonium ion is 2.4 kcal mol-1 more stable than the t-butyl cation, and that the substituent effect on its stability can be correlated with the Yukawa-Tsuno equation with a ρ value of -12.6 and an r+ of 0.62. An r+ value smaller than unity of the α-cumyl(1-methyl-1-phenylethyl) cation suggested that π-delocalization in the phenonium ion is essentially less effective than through a benzylic π-interaction. On the other hand, the ρ value of -12.6 is distinctly larger than that for the ordinary benzylic carbocation systems, but is comparable to that of the benzenium ion. In addition, it has been found that the r+ value of the phenonium ions in the gas phase is in complete agreement with that for the aryl-assisted process in the acetolysis of 2-arylethyl toluenesulfonates. This suggests that the degree of π-delocalization of the positive charge is the same in the transition state and the intermediate cation. It is concluded that an r+ value of 0.6, which is ranked at a unique position in the continuous spectrum of the resonance demand, is characteristic of the bridged structure of the phenonium ion intermediate and the transition state.
- Mustanir,Mishima, Masaaki,Fujio, Mizue,Tsuno, Yuho
-
p. 1401 - 1407
(2007/10/03)
-
- Triazolylated teritiary amine compound or salt thereof
-
A triazolylated tertiary amine compound represented by general formula (I) or a salt thereof, having an aromatase inhibitory activity and being useful for preventing and treating breast cancer, mastopathy, endometriosis, prostatomergaly, etc., wherein A represents a single bond, lower alkylene or carbonyl; B represents lower alkyl, aryl, a 5- or 6-membered heterocyclic group, or a bicyclic fused heterocyclic group; D represents aryl, a 5- or 6-membered heterocyclic group, or a bicyclic fused heterocyclic group; and E represents 4H-1,2,4-triazolyl, 1H-1,2,4-triazolyl or 1H-1,2,3-triazolyl.
- -
-
-
- Acridine orange derivatives and their use in the quantitation of reticulocytes in whole blood
-
Quaternized derivatives of acridine orange and reagents incorporating such derivatives and their use in quantitatively determining reticulocyte levels in whole blood specimen by fluorescence flow cytometry techniques are disclosed. The quaternized derivatives of acridine orange are of the general formula: STR1 wherein Y is bromide (Br-) or iodide (I-), and X may be R1 and/or R2 substituted benzyl group STR2 R1 is hydrogen or fluorine, and R2 is fluorine, trifluoromethyl or hydrogen, or X may be hydroxyl ethylene.
- -
-
-
- ORGANIC PHOSPHORUS COMPOUNDS 91. SYNTHESIS AND PROPERTIES OF 1-AMINO-2-ARYLETHYLPHOSPHONIC AND -PHOSPHINIC ACIDS AS WELL AS -PHOSPHINE OXIDES
-
The preparation, physical and spectroscopic properties of 1-amino-2-arylethylphosphonic, and -phosphinic acids as well as -phosphine oxides, the phosphorus analogues of phenylalanine are described, and the reactions of 1-amino-2-(4-fluorophenyl)ethylphosphonates with acetals, isocyanides, esters, acid anhydrides, activated aromatic nitro- and halogen compounds, and with N-protected alanine are reported.It is shown that several of the 1-amino-2-arylethylphosphonic acids are strong inhibitors of PAL and anthocyanin synthesis and also are quite active botryticides.Among the active compounds were 1-amino-2-(4-fluorophenyl)ethylphosphonic acid, 3f, and the methyl-substituted compounds 3k, 3l, and 3m.The fluoroderivative 3f was also effective as a seed-dressing agent in barley showing a 100percent protection against the fungus Fusarium nivale at 600 ppm.
- Maier, Ludwig
-
-
- 2-aryl-ethyl ether derivatives and insecticidal and acaricidal agents containing said derivatives
-
The present invention relates to 2-arylethyl ether or thioether derivatives represented by the following general formula [I]: STR1 wherein Ar stands for an aryl group, R1 stands for straight or branched chain alkyl group of 1 to 6 carbons, R2 stands for a hydrogen atom, or a methyl or ethyl group, R3 stands for a halogen atom, or a methyl or methoxyl group, R4 stands for a hydrogen or halogen atom, or a lower alkyl or lower alkoxy group, and n is an integer of 1 or 2 with the proviso that when n is 2, the groups R4 may be the same or different, and Y stands for an oxygen or sulfur atom, and also to processes for the preparation of these ethers or thioethers and a use of these ethers or thioethers. These compounds of the present invention have excellent insecticidal and acaricidal activities while the toxicity of these compounds are very low.
- -
-
-
- 2-Arylpropyl ether or thioether derivatives and insecticidal and acaricidal agents containing said derivatives
-
The present invention relates to 2-arylpropyl ether or thioether derivatives represented by the following general formula [I]: STR1 wherein Ar stands for an aryl group, R stands for a methyl or ethyl group, Y stands for an oxygen or sulfur atom, and B stands for a group represented by the following formula [II]: STR2 or the following general formula [III]: STR3 wherein Z stands for an oxygen or sulfur atom or a carbonyl or methylene group, R1 stands for a hydrogen or halogen atom or a lower alkyl group or a lower alkoxy group, and n is an integer of from 1 to 5 with the proviso that when n is 2 or more, the groups R1 may be the same or different, and also to processes for the preparation or these ethers of thioethers and a use of these ethers or thioethers. These compounds of the present invention have excellent insecticidal and acaricidal activities while the toxicity of these compounds are very low.
- -
-
-