cas 59-88-1, Phenylhydrazine hydrochloride

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REACTION OF SOME X-PHENYLAZIDES DERIVATIVES WITH DIETHYL 1,3-ACETONEDICARBOXYLATE
A series of ethyl 5-(2-ethoxy-2-oxoethyl)-1-(X-phenyl)-1H-1,2,3-triazole-4-carboxylate was synthesized through a condensation reaction of some aryl azides and diethyl-1,3-acetondicarboxylate (DEAD) in the presence of sodium ethoxide as a base. An unexpected heterocycle was isolated in the case of 2-trifluoromethylphenylazide. All the compounds are elucidated using FT-IR, NMR and MS spectroscopic techniques.
Fatmi, Chames Eddine,Bouasla, Souad,Teguiche, Mabrouk
p. 445 - 448
(2022/03/09)

Design, Synthesis, and Antifungal Activity of 2,6-Dimethyl-4-aminopyrimidine Hydrazones as PDHc-E1 Inhibitors with a Novel Binding Mode
A series of novel 2,6-dimethyl-4-aminopyrimidine hydrazones 5 were rationally designed and synthesized as pyruvate dehydrogenase complex E1 (PDHc-E1) inhibitors. Compounds 5 strongly inhibited Escherichia coli (E. coli) PDHc-E1 (IC50 values 0.94-15.80 μM). As revealed by molecular docking, site-directed mutagenesis, enzymatic, and inhibition kinetic analyses, compounds 5 competitively inhibited PDHc-E1 and bound in a "straight"pattern at the E. coli PDHc-E1 active site, which is a new binding mode. In in vitro antifungal assays, most compounds 5 at 50 μg/mL showed more than 80% inhibition against the mycelial growth of six tested phytopathogenic fungi, including Botrytis cinerea, Monilia fructigena, Colletotrichum gloeosporioides, andBotryosphaeria dothidea. Notably, 5f and 5i were 1.8-380 fold more potent against M. fructigena than the commercial fungicides captan and chlorothalonil. In vivo, 5f and 5i controlled the growth of M. fructigena comparably to the commercial fungicide tebuconazole. Thus, 5f and 5i have potential commercial value for the control of peach brown rot caused by M. fructigena.
Zhou, Yuan,Zhang, Shasha,Cai, Meng,Wang, Kaixing,Feng, Jiangtao,Xie, Dan,Feng, Lingling,Peng, Hao,He, Hongwu
p. 5804 - 5817
(2021/06/25)

Highly Efficient Synthesis of Hindered 3-Azoindoles via Metal-Free C-H Functionalization of Indoles
Although 3-azoindoles have recently emerged as an appealing family of photoswitch molecules, the synthesis of such compounds has been poorly covered in the literature. Herein a high-yielding and operationally simple protocol is reported allowing the synthesis of 3-azoindoles, featuring important steric hindrance around the azo motif. Remarkably, this C-H coupling is characterized by excellent atom economy and occurs under metal-free conditions, at room temperature, and within few minutes, delivering the expected products in excellent yields (quantitatively in most of the cases). Accordingly, a library of new molecules, with potential applications as photochromic compounds, is prepared.
Guillemard, Lucas,Jacob, Nicolas,Wencel-Delord, Joanna
supporting information
p. 574 - 580
(2020/02/13)

Allylic and Allenylic Dearomatization of Indoles Promoted by Graphene Oxide by Covalent Grafting Activation Mode
The site-selective allylative and allenylative dearomatization of indoles with alcohols was performed under carbocatalytic regime in the presence of graphene oxide (GO, 10 wt percent loading) as the promoter. Metal-free conditions, absence of stoichiometric additive, environmentally friendly conditions (H2O/CH3CN, 55 °C, 6 h), broad substrate scope (33 examples, yield up to 92 percent) and excellent site- and stereoselectivity characterize the present methodology. Moreover, a covalent activation model exerted by GO functionalities was corroborated by spectroscopic, experimental and computational evidences. Recovering and regeneration of the GO catalyst through simple acidic treatment was also documented.
Lombardi, Lorenzo,Bellini, Daniele,Bottoni, Andrea,Calvaresi, Matteo,Monari, Magda,Kovtun, Alessandro,Palermo, Vincenzo,Melucci, Manuela,Bandini, Marco
supporting information
p. 10427 - 10432
(2020/07/24)

Trimethoxyphenyl-containing evodiamine derivative and application thereof
According to the invention, the evodiamine compound is modified and optimized; wherein benzenetrimethoxy is introduced into an evodiamine skeleton; therefore, evodiamine and derivatives thereof are linked through amido bonds, and in-vitro and in-vivo antitumor activity screening experiments are carried out, so that a series of trimethoxyphenyl-containing evodiamine derivatives are synthesized, andhigh-efficiency and low-toxicity antitumor candidate drugs are screened out. The range of existing anticancer compounds is broadened, and the compounds can be used as lead compounds for continuous optimization; meanwhile, the compound has small toxic and side effects, does not have inhibitory activity on normal cells of a human body while inhibiting the growth of cancer cells, and is safer to use.
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Paragraph 0044; 0045; 0046

(2019/12/02)

DUAL INHIBITORS OF THE BCL-2 AND HDM2 FAMILIES THROUGH CO-MIMICRY OF THE BH3 AND P53-ALPHA-HELICES
The invention relates to dual HDM2/Bcl-2 inhibitors, providing a synergistic effect to help promote apoptosis in tumorigenic cells.
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Paragraph 0048

(2019/03/12)

Design, synthesis and biological evaluation of tryptamine salicylic acid derivatives as potential antitumor agents
A series of tryptamine salicylic acid derivatives were synthesized and their antiproliferative activity against MGC-803, MCF-7, HepG2, A549 and HeLa cell lines was evaluated. The structure-activity relationship (SAR) study revealed that different substitutions of the C5 and C3′-C5′ positions have certain effects on the anti-proliferation activity. The growth assay revealed that N-[2-(5-bromo-1H-indol-3-yl)-ethyl]-2-hydroxy-3-methyl-benzamide (E20) showed the most potent and broad-spectrum anticancer inhibition of all the cell lines evaluated, and was only more potent than 5-Fu for the gastric cancer cell line. Preliminary studies indicated that compound E20 could inhibit colony formation and migration of MGC-803 cells. The flow cytometry (FCM) results showed that compound E20 arrested the cell cycle in the G2/M phase and induced apoptosis of MGC-803 cells in a concentration-dependent manner. In addition, the western blot results showed that E20 can down-regulate the expression of hexokinase 2. Our studies suggest that the framework of N-[2-(5-bromo-1H-indol-3-yl)-ethyl]-2-hydroxy-3-methyl-benzamide may be consider as a new type of chemical for designing effective anti-cancer drugs targeting gastric cancer cells.
Xiong, Runde,He, Dongxiu,Deng, Xiangping,Liu, Juan,Lei, Xiaoyong,Xie, Zhizhong,Cao, Xuan,Chen, Yanming,Peng, Junmei,Tang, Guotao
p. 573 - 583
(2019/04/30)

Synthesis and evaluation of indole derivatives as photosynthesis and plant growth inhibitors
Indole derivatives were synthetized based on the Fischer indole methodology using different phenyl hydrazine hydrochlorides and either cyclohexanone or 2-butanone. The pre- and post-emergent herbicidal activities were evaluated against Ipomoea grandifolia. A carbazole, 6-chloro-2,3,4,9-tetrahydro-1H-carbazole (3b), decreased the PIabs parameter by 32% and increased the cross-section related parameters, indicating the inactivation of the reaction center on photosystem II. Compound 3b acts as a post-emergent herbicide prototype since dry biomass was reduced by 50%, corroborating the fluorescence results. Comparing instead with a germination experiment, 2,3,4,9-tetrahydro-1H-carbazole (3a) was found to be the most effective agent, inhibiting seed germination by 22% and decreasing root length by 50%. The tetrahydrocarbazoles showed better results than indole derivatives potentially due to the presence of methylene groups at structures, which increase the compounds' lipophilicity and may facilitate their access to the plant. In addition, electron withdrawing groups on the aromatic ring were found to correlate with increased herbicide activity. Further optimization of this series towards the development of herbicides is ongoing.
Mendes, Mylla Cristie Da Silva,Fazolo, Bruno Rodrigues,De Souza, Jéssica Maria,De Vasconcelos, Leonardo Gomes,De Sousa Junior, Paulo Teixeira,Dall'Oglio, Evandro Luiz,Soares, Marcos Ant?nio,Sampaio, Olívia Moreira,Vieira, Lucas Campos Curcino
p. 1350 - 1358
(2019/06/19)

Discovery of 1,3,4-oxadiazol-2-one-containing benzamide derivatives targeting FtsZ as highly potent agents of killing a variety of MDR bacteria strains
The spread of infections caused by multidrug-resistant (MDR) pathogens, such as methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant S. aureus (VRSA), has created a need for new antibiotics with novel mechanisms of action. The bacterial division protein FtsZ has been identified as a novel drug target that can be exploited clinically. As part of an ongoing effort to develop FtsZ-targeting antibacterial agents, we describe herein the design, synthesis and bioactivity of six series of novel 1,3,4-oxadiazol-2-one-containing, 1,2,4-triazol-3-one-containing and pyrazolin-5-one-containing benzamide derivatives. Among them, compound A14 was found to be the most potent antibacterial agent, much better than clinical drugs such as ciprofloxacin, linezolid and erythromycin against all the tested gram-positive strains, particularly methicillin-resistant, penicillin-resistant and clinical isolated S. aureus. Subsequent studies on biological activities and docking analyses proved that A14 functioned as an effective compound targeting FtsZ. Preliminary SAR indicated a general direction for further optimization of these novel analogues. Taken together, this research provides a promising chemotype for developing newer FtsZ-targeting bactericidal agents.
Bi, Fangchao,Song, Di,Qin, Yinhui,Liu, Xingbang,Teng, Yuetai,Zhang, Na,Zhang, Panpan,Zhang, Nan,Ma, Shutao
p. 3179 - 3193
(2019/06/17)

Synthesis of Aryl Hydrazines via CuI/BMPO Catalyzed Cross-Coupling of Aryl Halides with Hydrazine Hydrate in Water
The N,N’-bis(2,6-dimethylphenyl)oxalamide was discovered as a powerful ligand for Cu-catalyzed cross-coupling of aryl halides with hydrazine hydrate, leading to the formation of a variety of aryl hydrazines at 80 oC in water under the assistance of K3PO4 and 4 mol% cetyltrimethylammonium bromide from aryl bromides and aryl iodides. Good to excellent yields were observed in most cases.
Kumar, Siripuram Vijay,Ma, Dawei
supporting information
p. 1003 - 1006
(2018/09/20)

Synthesis, in vitro Antimicrobial, and Cytotoxic Activities of New 1,3,4-Oxadiazin-5(6H)-one Derivatives from Dehydroabietic Acid
A series of new 1,3,4-oxadiazin-5(6H)-one derivatives (6a–n) of dehydroabietic acid were designed and synthesized as potential antimicrobial and antitumor agents. Their structures were characterized by IR, 1H NMR, 13C NMR, MS, and elemental analyses. All the title compounds were evaluated for their antimicrobial activity against four bacterial and three fungal strains using the serial dilution method. Among them, compound 6e showed the highest antibacterial activity against Bacillus subtilis with a minimum inhibitory concentration (MIC) value of 1.9 μg/mL. In addition, the in vitro cytotoxic activities of the title compounds were also assayed against three human carcinoma cell lines (MCF-7, SMMC-7721, and HeLa) through the MTT colorimetric method. As a result, compounds 6b, 6g, 6k, and 6m exhibited significant inhibition against at least one cell line with IC50 values below 10 μM. Compound 6m was especially found to be the most potent derivative with IC50 values of 2.26 ± 0.23, 0.97 ± 0.11, and 1.89 ± 0.31 μM against MCF-7, SMMC-7721, and HeLa cells, respectively, comparable to positive control etoposide.
Jin, Xiao-Yan,Zhang, Kang-Ping,Chen, Hao,Miao, Ting-Ting,Wang, Shi-Fa,Gu, Wen
p. 538 - 547
(2018/06/11)

Indolamide compound capable of selectively inhibiting gastric cancer cells
The invention discloses an indolamide compound capable of selectively inhibiting gastric cancer cells. The compound is capable of inhibiting the gastric cancer cells, particularly MGC-803 (human gastric cancer cells) cell strains, therefore the compound can be used as medicines for the selectively treatment of gastric cancer and has better developing prospect.
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Paragraph 0024

(2018/10/19)

Synthesis and biological evaluation of (1-aryl-1H-pyrazol-4-yl) (3,4,5-trimethoxyphenyl)methanone derivatives as tubulin inhibitors
A series of (1-aryl-1H-pyrazol-4-yl) (3,4,5-trimethoxyphenyl)methanones (8a-p, 9a-p) and ketoxime (10c) derivatives were designed and synthesized as antitubulin agents. All of the target compounds were evaluated for the in vitro anti-proliferative activities against three tumor cell lines (A549, HT-1080, SGC-7901). The most promising compounds in this class were (1-(p-tolyl)-1H-pyrazol-4-yl) (3,4,5-trimethoxyphenyl)methanone (9c) and its ketoxime derivative (10c), which significantly inhibited tumor cells growth with IC50 value of 0.054–0.16 μM. Meanwhile, compound 9c exhibited effectively inhibitory activity of tubulin polymerization. Consistent with its antitubulin activity, compound 9c could destructively damage microtubule network and arrest SGC-7901 cell cycle at G2/M phase significantly. The structure-activity relationship (SAR) and conformational analysis indicate that methyl group at C4-position of C-ring is critical for the activities and the amino group at the C5-position of B-ring plays a negative role in maintaining bioactivity. Furthermore, a molecular docking study was performed to elucidate its binding mode at the colchicine site in the tubulin heterodimer.
Zhai, Min'an,Wang, Long,Liu, Shiyuan,Wang, Lijing,Yan, Peng,Wang, Junfang,Zhang, Jingbo,Guo, Haifei,Guan, Qi,Bao, Kai,Wu, Yingliang,Zhang, Weige
p. 137 - 147
(2018/07/13)

A class of 1, 5 - diphenyl pyrazole - 3 - carboxylic acid compound and use thereof
The invention provides a 1, 5-diphenyl pyrazol-3-carboxylic acid compound and application thereof. The compound has a structure as shown in general formula I, wherein R1 is selected from -H, halogen, saturated alkyl of C1-C6, or -X1-R4; R2 is selected from H, halogen, saturated alkyl of C1-C6, or -X2-R5; R3 is selected from H, -NH2 or -NH-CO-Ph-(o, m, p)R6; R6 is selected from H, halogen, saturated alkyl of C1-C6, or -O-R7; X1 and X2 are respectively selected from O or S independently; R4, R5 and R7 are respectively selected from H, saturated alkyl of C1-C6, benzyl or phenyl substituted by saturated alkyl of C1-C6 independently. The compound provided by the invention simulates BH3-only and p53TAD protein alpha-helix at the same time, competitively binds and antagonize Mcl-1, Bcl-2 and MDM2 protein, and specifically causes tumor cell apoptosis, thereby realizing application as an anticancer compound. (general formula I).
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Paragraph 0058; 0060

(2017/10/31)

Compounding method for edaravone
The invention belongs to the field of chemical compounding and particularly relates to a compounding method for edaravone. The compounding method comprises the following steps: (1) by taking aniline as a raw material, performing diazotization, reduction and acidification processes, thereby acquiring phenylhydrazine hydrochloride; (2) adjusting pH of phenylhydrazine hydrochloride, and then directly carrying out contracting ring-closure reaction with ethyl acetoacetate, without adding any other solvents in this process, thereby acquiring the product edaravone. According to the compounding method provided by the invention, aniline with lower cost is taken as the initial raw material, phenylhydrazine hydrochloride is firstly compounded, and then phenylhydrazine hydrochloride and ethyl acetoacetate directly have contracting ring-closure reaction under a backflow condition so as to compound edaravone, no solvent is added, a large amount of pollution discharge quantity in the middle link is reduced and the raw material cost is lowered. According to the compounding method provided by the invention, the raw materials are simple, the cost is lower, the reaction condition is mild, the reaction is almost quantitatively completed, the acquired edaravone crude product is higher in purity, the edaravone crude product can meet the medicinal standard after the simple recrystallization process, and the compounding method is suitable for the requirement of industrial production.
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Paragraph 0019; 0020; 0028; 0029; 0035-0036; 0042-0043

(2017/06/02)

A phenyl hydrazine preparation method (by machine translation)
The invention discloses a phenyl hydrazine preparation method, the method is a chloramine is reacted with aniline for preparing phenyl hydrazine hydrochloride, then the phenyl hydrazine hydrochloride in the lye and get the arylhydrazines. With the traditional diazotization reaction process for preparing arylhydrazines compared with the method of, the invention adopts the method of the mild reaction conditions, few reaction steps, the operation is simple, few by-products, low energy consumption, high yield, little consumption of raw materials, the production cost is low, it is a kind of energy saving and environment protecting the new process. (by machine translation)
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Paragraph 0005; 0008; 0009; 0010

(2017/08/30)

Rh(II)-catalyzed intramolecular annulation of N-sulfonyl 1,2,3-triazoles with indole derivatives: A new method for synthesis pyranoindoles
A direct and highly stereoselective approach for the synthesis of Z-alkenyl-pyranoindoles had been developed by utilizing Rh(II)-catalyzed intramolecular cyclization of N-sulfonyl-1,2,3-triazoles with indole derivatives. A variety of pyranoindoles were obtained in 44-93% yields. Moreover, a more convenient synthesis of pyranoindoles starting from terminal alkyne was realized via a Cu-Rh sequentially catalyzed one-pot cascade reaction.
Xie, Hui,Yang, Jian-Xin,Bora, Pranjal Protim,Kang, Qiang
supporting information
p. 3014 - 3021
(2016/05/19)

Acylaminoimidazole derivative and use thereof
The invention belongs to the technical field of medicines and relates to an acylaminoimidazole derivative shown in the general formula I and its stereisomer and pharmaceutical acceptable salt, hydrate, solvate or prodrug. In the formula I, substituents R, R1, Ar, M and X are defined in the specification. The invention also relates to a method for preparing the compound shown in the formula I, a medicinal composition containing the compound and a use of the compound and the medicinal composition in preparation of drugs for treating and/or preventing cancers and other skin proliferative diseases. An antifungal experiment proves that the compound has strong resistance to shallow and deep fungi and can be used for preparation of an antibacterial drug.
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Paragraph 0632; 0633

(2016/10/07)

Bcl-2/MDM2 Dual Inhibitors Based on Universal Pyramid-Like α-Helical Mimetics
No α-helical mimetic that exhibits Bcl-2/MDM2 dual inhibition has been rationally designed due to the different helicities of the α-helixes at their binding interfaces. Herein, we extracted a one-turn α-helix-mimicking ortho-triarene unit from o-phenylene foldamers. Linking benzamide substrates with a rotatable C-N bond, we constructed a novel semirigid pyramid-like scaffold that could support its two-turn α-helix mimicry without aromatic stacking interactions and could adopt the different dihedral angles of the key residues of p53 and BH3-only peptides. On the basis of this universal scaffold, a series of substituent groups were installed to capture the key residues of both p53TAD and BimBH3 and balance the differences of the bulks between them. Identified by FP, ITC, and NMR spectroscopy, a compound 6e (zq-1) that directly binds to Mcl-1, Bcl-2, and MDM2 with balanced submicromolar affinities was obtained. Cell-based experiments demonstrated its antitumor ability through Bcl-2/MDM2 dual inhibition simultaneously.
Wang, Ziqian,Song, Ting,Feng, Yingang,Guo, Zongwei,Fan, Yudan,Xu, Wenjie,Liu, Lu,Wang, Anhui,Zhang, Zhichao
supporting information
p. 3152 - 3162
(2016/05/19)

A diversity-oriented approach to indolocarbazoles: Via Fischer indolization and olefin metathesis: Total synthesis of tjipanazole D and i
New synthetic strategies to indolocarbazoles have been reported via two-fold Fischer indolization under green conditions using l-(+)-tartaric acid and N,N-dimethyl urea. Starting with cyclohexanone, a bench-top starting material, this methodology has been extended to the total synthesis of natural products such as tjipanazoles D and I as well as the core structure of asteropusazole and racemosin B. Here, atom economical reactions like ring-closing metathesis, enyne-metathesis, and the Diels-Alder reaction have been used as key steps. Diverse strategies demonstrated here are useful in medicinal chemistry and materials science to design a library of decorated indoles.
Kotha, Sambasivarao,Saifuddin, Mohammad,Aswar, Vikas R.
supporting information
p. 9868 - 9873
(2016/10/31)

Design, synthesis, and biological evaluation of amide imidazole derivatives as novel metabolic enzyme CYP26A1 inhibitors
All-trans-retinoic acid (ATRA) as a physiological metabolite of vitamin A is widely applied in the treatment of cancer, skin, neurodegenerative and autoimmune diseases. CYP26A1 enzyme, induced by ATRA in liver and target tissues, metabolizes ATRA into 4-hydroxyl-RA. Inhibition of CYP26A1 metabolic enzyme represents a promising strategy for discovery of new specific anticancer agents. Herein, we describe the design, synthesis and biological evaluation of a series of new amide imidazole derivatives as retinoic acid metabolism blocking agents (RAMBAs) toward CYP26A1 enzyme. First, based on the recent theoretical models (Sun et al., J. Mol. Graph. Model., 2015, 56, 10-19) a series of RAMBAs with novel scaffolds were designed using fragment-based drug discovery approach. Subsequently, the new RAMBAs were synthesized and evaluated for their biological activities. All the compounds demonstrated appropriate enzyme activities and cell activities. The promising inhibitors 20 and 23 with IC50 value of 0.22 μM and 0.46 μM toward CYP26A1, respectively, were further evaluated for CYP selectivity and the metabolic profile of ATRA. Both compounds 20 and 23 showed higher selectivity for CYP26A1 over other CYPs (CYP2D6, CYP3A4) when compared to liarozole. They also showed better inhibitory activities for the metabolism of ATRA when also compared to liarozole. These studies further validated the pharmacophore and structure-activity relationship models obtained about CYP26A1 inhibitors and highlighted the promising activities of the new series of CYP26A1 inhibitors designed from such models. They also paved the way for future development of those candidates as potential drugs.
Sun, Bin,Liu, Kai,Han, Jing,Zhao, Li-Yu,Su, Xiao,Lin, Bin,Zhao, Dong-Mei,Cheng, Mao-Sheng
p. 6763 - 6773
(2015/10/20)

Rhodium(III)-catalyzed in situ oxidizing directing group- assisted c-h bond activation and olefination: A route to 2-vinylanilines
A new and efficient method for the synthesis of 2-vinylanilines from the reaction of arylhydrazine hydrochlorides with alkenes and diethyl ketone via a rhodium-catalyzed C-H activation is described. The oxidant-free olefination reaction involves the in situ generation of an -N-N=CR1R2 moiety as the oxidizing directing group thus providing an easy access to 2-vinylanilines.
Muralirajan, Krishnamoorthy,Haridharan, Radhakrishnan,Prakash, Sekar,Cheng, Chien-Hong
supporting information
p. 761 - 766
(2015/03/18)

Synthesis and biological evaluation of 3-alkyl-1,5-diaryl-1H-pyrazoles as rigid analogues of combretastatin A-4 with potent antiproliferative activity
A series of novel 3-alkyl-1,5-diaryl-1H-pyrazoles were synthesized as combretastatin A-4 (CA-4) analogues and evaluated for antiproliferative activity against three human cancer cell lines (SGC-7901, A549 and HT-1080). Most of the target compounds displayed moderate to potent antiproliferative activity, and 7k was found to be the most potent compound. Structure-activity relationships indicated that compounds with a trimethoxyphenyl A-ring at the N-1 position of the pyrazole skeleton were more potent than those with the A-ring at the C-5 position. Tubulin polymerization and immunostaining experiments revealed that 7k potently inhibited tubulin polymerization and disrupted tubulin microtubule dynamics in a manner similar to CA-4. Computational modelling demonstrated that the binding of 7k to the colchicine binding site on microtubules may involve a similar mode as CA-4.
Xu, Qile,Qi, Huan,Sun, Maolin,Zuo, Daiying,Jiang, Xuewei,Wen, Zhiyong,Wang, Zhiwei,Wu, Yingliang,Zhang, Weige
(2015/07/15)

Synthesis, fungicidal activity, structure-activity relationship and density functional theory studies of novel oxime ether derivatives containing 1-aryl-3-oxypyrazoles
A series of 16 oxime ether derivatives containing 1-aryl-3-oxypyrazoles were synthesised, and the structure of one of them, (E)-methyl 2-(2-({(1-(4-chlorophenyl)-1H-pyrazol-3-yl)-oxy}methyl)phenyl)-2-(methoxyimino)acetate was determined by X-ray diffraction crystallography. Preliminary bioassays indicated that some of these compounds exhibited very good fungicidal activities against Rhizoctonia solani, especially the ester 2-(2-({(1-(4-chlorophenyl)-1H-pyrazol-3-yl)-oxy}methyl)phenyl)-2-(methoxyimino)acetate, which displayed greater activity than control compound pyraclostrobin at a dosage of 0.1 μg mL-1. The relationship between structure and fungicidal activity was discussed. Density functional theory studies of the 3-methyl heterocyclic ester and the 4-chorophenyl heterocyclic N-methylamide were carried out and the results discussed in terms of the wide difference in fungicidal activity shown by each compound.
Lv, Kunzhi,Liu, Yuanyuan,Li, Yi,Xu, Guanghui,Pan, Xuechun,Li, Fangshi,Chen, Kai,Huang, Bin,Yang, Yaping
p. 594 - 600
(2015/11/27)

Facile and convenient synthesis of aryl hydrazines via copper-catalyzed C-N cross-coupling of aryl halides and hydrazine hydrate
An efficient and convenient method for the synthesis of aryl hydrazines has been developed via copper-catalyzed cross-coupling of aryl bromides and hydrazine with a readily accessible ligand and water as a solvent. The multigram scale procedure is applicable to aryl bromides bearing both moderately electron-donating and electron-withdrawing substituents in the aromatic nucleus. No column chromatography is required to obtain aryl hydrazine hydrochlorides in good yields.
Kurandina, Daria V.,Eliseenkov, Eugene V.,Ilyin, Petr V.,Boyarskiy, Vadim P.
p. 4043 - 4048
(2014/06/09)

Nickel-catalyzed N-arylation of benzophenone hydrazone with bromoarenes
A nickel-catalyzed method for the cross-coupling of benzophenone hydrazone with aryl bromides is described. The use of a simple Ni(ii)/NHC catalyst leads to the arylated hydrazones in good or acceptable yields. This protocol provides a simple, convenient alternative to the synthesis of arylhydrazines.
Wu, Wei,Fan, Xin-Heng,Zhang, Li-Peng,Yang, Lian-Ming
p. 3364 - 3367
(2014/01/06)

Design, synthesis, crystal structures, and insecticidal activities of eight-membered azabridge neonicotinoid analogues
Three series of novel azabridge neonicotinoid analogues were designed and synthesized, which were constructed by starting material A, glutaraldehyde, and primary amine hydrochlorides (aliphatic amines, phenylhydrazines, and anilines). Most of the eight-membered azabridge compounds presented higher insecticidal activities than oxabridged compound B against cowpea aphid (Aphis craccivora) and brown planthopper (Nilaparvata lugens). Compared with imidacloprid, some azabridged compounds exhibited excellent insecticidal activity against brown planthopper. The crystal structures and bioassay indicated that changing bridge atoms from O to N could lead to entirely different conformations, which might be the important influential factor of the bioactivities.
Xu, Renbo,Xia, Rui,Luo, Ming,Xu, Xiaoyong,Cheng, Jiagao,Shao, Xusheng,Li, Zhong
p. 381 - 390
(2014/02/14)

Regioselective synthesis of indoles via rhodium-catalyzed C-H activation directed by an in-situ generated redox-neutral group
A regioselective synthesis of indoles from arylhydrazine hydrochlorides with alkynes and diethyl ketone catalyzed by a rhodium complex is described. A possible mechanism involving an in-situ generated oxidizing directing group -N-Ni'CR1R2 assisted ortho-C-H activation and reductive elimination are proposed. The catalytic reaction is highly compatible with a wide range of functional arylhydrazines and alkynes. The reaction proceeds under mild reaction conditions and is atom-step economical.
Muralirajan, Krishnamoorthy,Cheng, Chien-Hong
p. 1571 - 1576
(2014/06/09)

Design, synthesis and pharmacological evaluation of 6,7-disubstituted-4- phenoxyquinoline derivatives as potential antitumor agents
Two series of 6,7-disubstituted-4-phenoxyquinoline derivatives bearing 2,4-imidazolinedione/pyrazolone scaffold were designed, synthesized and evaluated for their c-Met kinase inhibition and cytotoxicity against HT-29, H460, A549, MKN-45, and U87MG cancer cell lines in vitro. The pharmacological data indicated that most of the tested compounds showed moderate to significant cytotoxicity and high selectivity against HT-29, H460 and A549 cancer cell lines as compared with foretinib. The SAR analyses indicated that compounds with halogen groups, especially trifluoromethyl groups at 2-position on the phenyl ring (moiety B) were more effective. In this study, a promising compound 17 (c-Met IC50 = 2.20 nM, a multi-target tyrosine kinase inhibitor) showed the most potent antitumor activities with IC50 values of 0.14 μM, 0.18 μM, 0.09 μM, 0.03 μM, and 1.06 μM against HT-29, H460, A549, MKN-45, and U87MG cell lines, respectively.
Zhou, Shunguang,Ren, Jianguo,Liu, Mingmei,Ren, Lixiang,Liu, Yajing,Gong, Ping
p. 30 - 42
(2014/10/16)

Design, synthesis and pharmacological evaluation of 6,7-disubstituted-4-phenoxyquinoline derivatives as potential antitumor agents
Two series of 6,7-disubstituted-4-phenoxyquinoline derivatives bearing 2,4-imidazolinedione/pyrazolone scaffold were designed, synthesized and evaluated for their c-Met kinase inhibition and cytotoxicity against HT-29, H460, A549, MKN-45, and U87MG cancer cell lines in vitro. The pharmacological data indicated that most of the tested compounds showed moderate to significant cytotoxicity and high selectivity against HT-29, H460 and A549 cancer cell lines as compared with foretinib. The SAR analyses indicated that compounds with halogen groups, especially trifluoromethyl groups at 2-position on the phenyl ring (moiety B) were more effective. In this study, a promising compound 17 (c-Met IC50= 2.20 nM, a multi-target tyrosine kinase inhibitor) showed the most potent antitumor activities with IC50values of 0.14 μM, 0.18 μM, 0.09 μM, 0.03 μM, and 1.06 μM against HT-29, H460, A549, MKN-45, and U87MG cell lines, respectively.
Zhou, Shunguang,Ren, Jianguo,Liu, Mingmei,Ren, Lixiang,Liu, Yajing,Gong, Ping
p. 30 - 42
(2014/12/11)

Indole synthesis by rhodium(III)-catalyzed hydrazine-directed C-H activation: Redox-neutral and traceless by N-N bond cleavage
Fishing for complements! There is an alternative to the useful Fischer indole synthesis. The new method utilizes the same retrosynthetic disconnection but is based on a RhIII-catalyzed directed C-H activation step and a successive coupling with alkynes. Copyright
Zhao, Dongbing,Shi, Zhuangzhi,Glorius, Frank
supporting information
p. 12426 - 12429
(2013/12/04)

Design, synthesis and biological activities of novel benzoyl hydrazines containing pyrazole
In search of environmentally benign compounds with high biological activity, low toxicity and low resistance, 8 novel benzoyl hydrazines containing pyrazole were designed and synthesized. All compounds were characterized by 1H NMR spectra and HRMS. The preliminary results of biological activity assessment indicated that most of title compounds exhibited certain insecticidal activities against Mythimna separata Walker at 200 mg·L -1 but excellent fungicidal activities against six fungus at 50 mg·L-1, which were better than the control. Eight novel benzoyl hydrazines containing pyrazole were designed and synthesized. The preliminary results of biological activity assessment indicated that most of title compounds exhibited certain insecticidal activities against Mythimna separata Walker at 200 mg·L-1 but excellent fungicidal activities against six fungus at 50 mg·L-1, which were better than the control. Copyright
Yan, Tao,Yu, Shujing,Liu, Pengfei,Liu, Zhuo,Wang, Baolei,Xiong, Lixia,Li, Zhengming
scheme or table
p. 919 - 923
(2012/06/01)

Unusual course of reaction of buta-1,3-diene-1,4- diylbis(triphenylphosphonium chloride) with phenylhydrazine
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Ovakimyan,Movsisyan,Gasparyan,Indzhikyan
experimental part
p. 444 - 446
(2011/06/26)

Copper-mediated synthesis of substituted 2-aryl-N-benzylbenzimidazoles and 2-arylbenzoxazoles via C-H functionalization/C-N/C-O bond formation
An efficient method for the transformation of N-benzyl bisarylhydrazones and bisaryloxime ethers to functionalized 2-aryl-N-benzylbenzimidazoles and 2-arylbenzoxazoles is described. The protocol involves a copper(II)-mediated cascade C-H functionalization/C-N/C-O bond formation under neutral conditions. Substrates having either electron-donating or -withdrawing substituents undergo the cyclization to afford the target heterocycles at moderate temperature.
Guru, Murali Mohan,Ali, Md Ashif,Punniyamurthy, Tharmalingam
scheme or table
p. 5295 - 5308
(2011/08/05)

Synthesis and antimicrobial activities of novel 1H-dibenzo[a,c]carbazoles from dehydroabietic acid
A series of novel 1H-dibenzo[a,c]carbazole derivatives were synthesized in good yield through reaction of methyl 7-oxo-dehydroabietate with a variety of substituted phenylhydrazines. The structures of the newly synthesized compounds were confirmed by IR, 1H NMR, MS spectral studies and elemental analysis. All compounds were investigated for their activity against four bacteria (Bacillus subtilis, Staphylococcus aureus, Escherichia coli and Pseudomonas fluorescens) and three fungi (Trichophyton rubrum, Candida albicans and Aspergillus niger). Among the compound tested, 6d, 6e, 6f and 6m exhibited pronounced antibacterial activities and 6e and 6m also showed moderate antifungal activities. Particularly, 6d exhibited stronger antibacterial activity against B. subtilis comparable to positive control.
Gu, Wen,Wang, Shifa
experimental part
p. 4692 - 4696
(2010/10/03)

Synthesis, crystal structure, and fungicidal activity of novel 1,5-Diaryl-1H-pyrazol-3-oxyacetate derivatives
A series of ethyl 2-(1,5-diaryl-1H-pyrazol-3-yloxy)acetate derivatives (5a-5i) have been efficiently synthesized by the reaction of 1,5-diaryl-1H-pyrazol-3-ols (4a-4i) with ethyl 2-bromoacetate. The structures of the newly synthesized compounds were characterized by 1H NMR spectra and elemental analysis, and the crystal structure of the compound ethyl 2-(5-(4-chlorophenyl)-1-phenyl-1H-pyrazol-3-yloxy)acetate (5c) was determined by single crystal X-ray diffraction analysis. The compound 5c belongs to triclinic system with space group P(-1), a = 5.8170(12) A, b = 11.804(2) A, c = 12.783(2) A, α = 83.89(2)°, β = 89.24(3)°, γ = 89.73(3)°, Formula weight: 356.80, Triclinic V = 872.7(3) A3, Dc = 1.358 mg/m3, Z = 2, F (000) = 372. Bioassay results indicated that the compound ethyl 2-(5-(4-fluorophenyl)-1- phenyl-1H-pyrazol-3-yloxy)acetate (5d) exhibited moderate inhibitory activity against Gibberella zeae at the dosage of 10 μg/mL.
Liu, Yuanyuan,Shi, Hong,Li, Yufeng,Zhu, Hongjun
scheme or table
p. 897 - 902
(2010/10/18)

Synthesis, crystal structure and fungicidal activities of new type oxazolidinone-based strobilurin analogues
A series of oxazolidinone-based strobilurin analogues were efficiently synthesized by the reaction of 3-(2-bromomethylphenyl) oxazolidin-2-one with 1-substituted phenyl-2H-pyrazolin-3-one. Their structures were confirmed and characterized by 1H-NMR, 13C-NMR, elemental analysis, and mass spectroscopy. In addition, the crystal structure of the target compound 3-(2-((1-phenyl-2H-pyrazol-3-yloxy)methyl)phenyl) oxazolidin-2-one was determined by single crystal X-ray diffraction. The bioassay results of these compounds indicated that some of the oxazolidin-2-one derivatives containing N-substituted phenyl 2H-pyrazol ring exhibited potential in vivo fungicidal activities against M. grisea at the dosage of 1 g L-1.
Li, Yuhao,Liu, Rui,Yan, Zhangwei,Zhang, Xiangning,Zhu, Hongjun
experimental part
p. 3341 - 3347
(2012/05/05)

Synthesis and structure of indoline spiropyrans of the coumarin series
New indoline spiropyrans of the coumarin series were synthesized by the condensation of indoline and hydroxyformylcoumarin derivatives. Spiropyrans, viz., derivatives of 8-formyl-7-hydroxy-4-methylcoumarin and 5-formyl-6-hydroxy-4-methylcoumarin, under irradiation are transformed into open forms, which are recyclized in the dark. The compounds formed by the condensation of the indoline derivatives with 3-formyl-4-hydroxycoumarin have an open structure of the merocyanine dyes and are transformed into spiro forms neither in the dark nor under irradiation with the visible light.
Traven,Miroshnikov,Chibisova,Barachevsky,Venidiktova,Strokach
p. 2417 - 2424
(2007/10/03)

Synthesis of β3 adrenergic receptor agonist LY377604 and its metabolite 4-hydroxycarbazole, labeled with carbon-14 and deuterium
Synthesis of 14C-radiolabeled 4-hydroxycarbazole was accomplished starting from aniline-[U-14C], based on zinc chloride initiated Fischer cyclization of the phenylhydrazone prepared from phenylhydrazine-[U-14C] and cyclohexane-1,3-dione. The resulting tetrahydrooxocarbazole was subjected to dehydrogenation-aromatization using palladium on carbon. The aromatized 4-hydroxycarbazole-[4b,5,6,7,8,8a- 14C] was then used for the synthesis of 14C-labeled β3 adrenergic receptor agonist LY377604. The introduction of four deuteria in the carbazole fragment of LY377604 accomplished by its initial bromination and subsequent catalytic deuteration of the resulting tetrabromide. A similar approach was used for the conversion of 4-hydroxycarbazole into its tetradeutero-isotopomer. Copyright
Czeskis, Boris A.,Wheeler, William J.
p. 407 - 419
(2007/10/03)

Syntheses of α-Haloformylarylhydrazines and Their Self-dimerizations
α-Haloformylarylhydrazine hydrohalides 1 were prepared through ring opening of 3-aryl-4-halosydnones 7 with hydrohalic acids in EtOAc in moderate yields.Reactions between compounds 1 and primary alcohols gave alkyl 1-arylhydrazinecarboxylates 12 and 14, important intermediates in syntheses of antiinflammatory drugs.Compounds, 16, 4-aryl-2-(arylhydrazin-1-yl)-1,3,4-oxadiazolin-5-ones, and compounds 18, 1,4-diaryl-1,4-dihydro-1,2,4,5-tetrazine-3,6-(2H,5H)-diones, were synthesized by self-dimerization of compounds 1.Compounds 18 were also converted to compounds 17 via intramolecular rearrangement.Structural elucidation and verification of the reaction mechanisms are presented.Key Words 3-Aryl-4-halosydnone; α-Haloformylarylhydrazine hydrohalide; Acid hydrolysis; Self-dimerization; Intramolecular rearrangement.
Kuo, C. N.,Wu, M. H.,Chen, S. P.,Li, T. P.,Huang, C. Y.,Yeh, M. Y.
p. 849 - 856
(2007/10/03)

Process for the preparation of indazoles
A process for the preparation of aryl hydrazines and indazoles by reacting organometallic regents with azodicarboxylates.
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(2008/06/13)

ADDITION OF ARYLMETALLICS TO AZODICARBOXYLATES: A NOVEL SYNTHESIS OF ARYLHYDRAZINES BY AROMATIC HYDRAZINATION
Aryllithiums and arylmagnesium bromides add to the N=N bond of di-t-butyl azodicarboxylate, and subsequent acid deprotection provides the arylhydrazine.
Demers, James P.,Klaubert, Dieter H.
p. 4933 - 4934
(2007/10/02)

Indole-5-acetamides for treatment of migraine
Compounds are disclosed of general formula (I): STR1 wherein R1, R3, R4, R6 and R7, which may be the same or different, each represents a hydrogen atom or an alkyl group; R2 represents a hydrogen atom or an alkyl, aryl, aralkyl, cycloalkyl or alkenyl group; or R1 and R2, together with the nitrogen atom to which they are attached, form a saturated monocyclic 5 to 7-membered ring which may optionally contain a further hetero function; R5 represents a hydrogen atom or an alkyl or alkenyl group; or R4 and R5 together form an aralkylidene group; Alk represents an alkylene chain containing two or three carbon atoms which may be unsubstituted or substituted by not more than two C1-3 alkyl groups; and X represents an oxygen or sulphur atom; and physiologically acceptable salts, solvates and bioprecursors thereof. The compounds are described as potentially useful for the treatment of migraine and may be formulated as pharmaceutical compositions in conventional manner using one or more pharmaceutically acceptable carriers or excipients. Various processes for the preparation of the compounds are disclosed including, for example, a process involving reacting an indole having an appropriate nitrile group at the 5-position, with a suitable oxygen- or sulphur-containing compound in order to introduce the required amide or thioamide group at the 5-position on the indole nucleus.
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(2008/06/13)

Process for the preparation of arylhydrazine-N-sulfonic acids
The invention relates to a process for the preparation of arylhydrazine-N-sulfonic acids by reduction of aryldiazosulfonates with hydrogen in the presence of transition metal catalysts.
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(2008/06/13)

THIOSULFONIC ACIDS. XXXI. ARYLAZOARENETHIOSULFONATES
Arylazoarenethiosulfonates were obtained, and their structures and chemical characteristics were studied.It was shown that arylazoarenethiosulfonates have a nonionic structure, and this explains their high stability.It was established that they enter with difficulty into reactions with the release of nitrogen, but they enter readily into azo-coupling and reduction reactions.
Boldyrev, B. G.,Grivnak, L. M.
p. 324 - 330
(2007/10/02)