- N-Amino-1,8-Naphthalimide is a Regenerated Protecting Group for Selective Synthesis of Mono-N-Substituted Hydrazines and Hydrazides
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A new route to synthesis of various mono-N-substituted hydrazines and hydrazides by involving in a new C?N bond formation by using N-amino-1,8-naphthalimide as a regenerated precursor was invented. Aniline and phenylhydrazines are reproduced upon reacting these individually with 1,8-naphthalic anhydride followed by hydrazinolysis. The practicality and simplicity of this C?N dihalo alkanes; developed a synthon for bond formation protocol was exemplified to various hydrazines and hydrazides. N-amino-1,8-naphthalimide is suitable synthon for transformation for selective formation of mono-substituted hydrazine and hydrazide derivatives. Those are selective mono-amidation of hydrazine with acid halides; mono-N-substituted hydrazones from aldehydes; synthesis of N-aminoazacycloalkanes from acetohydrazide scaffold and inserted to hydroxy derivatives; distinct synthesis of N,N-dibenzylhydrazines and N-benzylhydrazines from benzyl halides; synthesis of N-amino-amino acids from α-halo esters. Ecofriendly reagent N-amino-1,8-naphthalimide was regenerated with good yields by the hydrazinolysis in all procedures.
- Manoj Kumar, Mesram,Venkataramana, Parikibanda,Yadagiri Swamy, Parikibanda,Chityala, Yadaiah
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supporting information
p. 17713 - 17721
(2021/11/10)
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- Iron-catalyzed oxidative amidation of acylhydrazines with amines
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A new approach for amide bond formation via a mild and efficient Iron-catalyzed cross-coupling reaction of acylhydrazines and amines using TBHP as oxidant is described. This protocol is compatible with a wide range of amines and acylhydrazines. In addition, the synthetic application of the reaction is presented.
- Wang, Yi-Jie,Zhang, Guo-Yu,Shoberu, Adedamola,Zou, Jian-Ping
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supporting information
(2021/08/18)
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- Design, Synthesis, and Study of the Insecticidal Activity of Novel Steroidal 1,3,4-Oxadiazoles
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A series of novel steroidal derivatives with a substituted 1,3,4-oxadiazole structure was designed and synthesized, and the target compounds were evaluated for their insecticidal activity against five aphid species. Most of the tested compounds exhibited potent insecticidal activity against Eriosoma lanigerum (Hausmann), Myzus persicae, and Aphis citricola. Compounds 20g and 24g displayed the highest activity against E. lanigerum, showing LC50 values of 27.6 and 30.4 μg/mL, respectively. Ultrastructural changes in the midgut cells of E. lanigerum were detected by transmission electron microscopy, indicating that these steroidal oxazole derivatives might exert their insecticidal activity by destroying the mitochondria and nuclear membranes in insect midgut cells. Furthermore, a field trial showed that compound 20g exhibited effects similar to those of the positive controls chlorpyrifos and thiamethoxam against E. lanigerum, reaching a control rate of 89.5% at a dose of 200 μg/mL after 21 days. We also investigated the hydrolysis and metabolism of the target compounds in E. lanigerum by assaying the activities of three insecticide-detoxifying enzymes. Compound 20g at 50 μg/mL exhibited inhibitory action on carboxylesterase similar to the known inhibitor triphenyl phosphate. The above results demonstrate the potential of these steroidal oxazole derivatives to be developed as novel pesticides.
- Bai, Hangyu,Jiang, Weiqi,Li, Qi,Li, Tian,Ma, Shichuang,Shi, Baojun,Wu, Wenjun
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p. 11572 - 11581
(2021/10/12)
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- Fragment-based drug discovery of triazole inhibitors to block PDEδ-RAS protein-protein interaction
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Although mutated Ras protein is well recognized as an important drug target, direct targeting Ras has proven to be a daunting task. Recent studies demonstrated that Ras protein needs PDEδ to relocate to plasma membrane to execute its signaling transduction function, which provides a new avenue for modulating the Ras protein. To find small molecules antagonizing the interactions between PDEδ and Ras, here we presented a successful application of fragment-based drug discovery of PDEδ inhibitors. Under the guidance of crystal structures, we are able to quickly optimize the initial fragment into highly potent inhibitors, with more than 2000-fold improvement in binding activity, which further adds to the arsenal towards the inhibition of Ras signaling in cancer therapy.
- Chen, Danqi,Chen, Yuehong,Lian, Fulin,Chen, Liu,Li, Yanlian,Cao, Danyan,Wang, Xin,Chen, Lin,Li, Jian,Meng, Tao,Huang, Min,Geng, Meiyu,Shen, Jingkang,Zhang, Naixia,Xiong, Bing
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p. 597 - 609
(2019/01/04)
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- Synthetic method of 1,3,4-thiadiazole derivative
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The invention discloses a synthetic method of a 1,3,4-thiadiazole derivative. The method comprises the following steps: (1) using hydrazine hydrate as a raw material, under the action of a catalyst, reacting with acid, to obtain a hydrazide compound I; (2) using alkyl chloroformate and thiocyanate to react in a condition of a solvent, to obtain an isothiocyanate compound II; (3) in a reaction system of the isothiocyanate compound II, adding solution containing the compound I, reacting to obtain solution containing a compound III; (4) processing the solution of the compound III by dehydrating,neutralizing, and washing, to obtain a compound IV; (5) in the conditions of an acid-binding agent and a solvent, adding alkyl halide or sulfuric acid diester into the compound IV, reacting to obtaina compound V; and (6) enabling the compound V to perform an amination reaction with primary amine, to obtain the 1,3,4-thiadiazole derivative VI. The preparation method has the advantages of green andno pollution, simple and convenient operation, higher yield, mild reaction condition and the like.
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Paragraph 0059; 0060
(2018/12/05)
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- Asymmetric Synthesis and Antitumor Activity of Spiro-Oxadiazole Derivatives from 1,4:3,6-Dianhydro-D-fructose
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A series of spiro-oxadiazoles were synthesized from 1,4:3,6-dianhydro-D-fructose and hydrazides via a stereo- selective two-step reaction sequence. The structures of newly synthesized compounds were established by spectral analysis. The absolute configuration of compound 2a was further confirmed by single crystal X-ray analysis. All the synthesized compounds were screened for their in vitro antitumor activity, showing that these compounds have poor inhibitory activities against A549, MGC-803 tumor cells.
- Xu, Wenke,Ge, Yongxun,Hou, Yu,Liu, Yingju,Hua, Yingchun,Han, Weiwei,Qin, Zhiyan,Liu, Fengwu
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p. 1437 - 144
(2017/10/06)
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- SUBSTITUTED AMINOPYRIMIDINE COMPOUNDS AND METHODS OF USE
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The invention relates to the preparation and use of new aminopyrimidine derivatives as drug candidates in free form or in pharmaceutically acceptable salt form and formulations thereof for the modulation of a disorder or disease which is mediated by the activity of the PI3K enzymes. The invention also provides pharmaceutically acceptable compositions comprising such compounds and methods of using the compositions in the treatment of disorders or diseases, such as disorders of immunity and inflammation in which PI3K enzymes play a role in leukocyte function, and hyperproliferative disorders associated with PI3K activity, including but not restricted to leukemias and solid tumors, in mammals, especially humans.
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Paragraph 368
(2016/10/04)
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- Substituted aminopyrimidine compound and usage method and application thereof
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The present invention relates to a substituted aminopyrimidine compound and a usage method and application thereof, and in particular to application of the novel aminopyrimidine compound and free-form salts or pharmaceutically acceptable salts and preparations thereof as the medicaments for the treatment of PI3-kinase abnormality-related disorder or diseases. The invention also relates to the pharmaceutical compositions comprising the compound, and application of the pharmaceutical compositions to the treatment of mammals, particularly for the treatment of PI3-kinase abnormality-related human disorder or diseases, such as treatment of PI3-kinase regulated immune and inflammatory diseases, wherein PI3-kinase plays a major role in leukocyte function, and the treatment of of PI3- kinase-related proliferative diseases including but not limited to leukemia and solid tumors.
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Paragraph 0702; 0703; 0704
(2017/07/20)
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- Crystal structure, DFT theoretical study and herbicidal activity of novel 1,2,4-triazole compound containing cyclopropyl group
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A novel 1,2,4-triazole compound was synthesized and the chemical structure was confirmed by 1H NMR, MS and elemental analyses. The crystal structure of the 1,2,4-triazole (C13H14FN3S, Mr = 263.33) has been determined by single-crystal X-ray diffraction. The compound crystallizes in the monoclinic system, space group P2(1)/c with a = 7.5179(15), b = 19.638(4), c = 8.4922(17)?, α = 90°, β = 98.11(3)°, γ = 90°, V = 1241.2(4)?3, Z = 4,. The herbicidal activity of 1,2,4-triazole was determined and the results showed the title compound displayed excellent herbicidal activity. Theoretical calculations of 1,2,4-triazole was carried out with B3LYP/6-31G (d,p) approximation. The optimized geometric parameters obtained by using DFT method show the best agreement with the experimental data.
- Sun, Guo-Xiang,Yang, Ming-Yan,Zhao, Wen,Sun, Zhao-Hui,Wu, Hong-Ke
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p. 567 - 573
(2015/08/04)
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- Synthesis of 3-hydroxyindanones via potassium salt of amino acid catalyzed regioselective intramolecular aldolization of ortho-diacylbenzenes
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First organocatalytic intramolecular aldolization of ortho-diacylbenzenes to construct highly functionalized 3-hydroxyindanones is described. In this transformation a high trans-selectivity is achieved by the use of metal salt of amino acid. This method allows an easy access to the strained spirocyclic 3-hydroxyindanones related to a number of natural product frameworks. Synthesis of a new class of indole skeleton substituted by 3-hydroxyindanones added an extra essence to this new protocol.
- Chanda, Tanmoy,Chowdhury, Sushobhan,Anand, Namrata,Koley, Suvajit,Gupta, Ashutosh,Singh, Maya Shankar
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supporting information
p. 981 - 985
(2015/03/04)
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- Crystal structure, DFT calculations and herbicidal activity of a new 1,2,3-triazole derivative containing sulfonyl group
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A new 1,2,4-triazole with sulfonyl moiety was synthesized and confirmed by 1H-NMR, MS and elemental analyses. The crystal structure of the title compound 5 (C13H14FN3SO2, Mr = 295.33) was determined by single-crystal X-ray diffraction. The crystal structure of this compound is triclinic, space group P-1 with a = 7.3111(15), b = 8.8637(18), c = 11.514(2) A, α = 69.09(3)°, β = 80.17(3)°, γ = 72.08(3)°, V = 661.6(2) A3, Z = 2, F(000) = 308, Dc = 1.482 g/cm3, μ = 0.262 mm-1, the final R1 = 0.0292 and wR2 = 0.0848 for 1960 observed reflections with I > 2?(I). A total of 4393 reflections were collected, of which 2305 were independent (Rint = 0.0223). The herbicidal activity of the triazole was moderate against rape root and barn-yard grass. Theoretical calculations of the title compound were carried out using B3LYP with the 6-31++G (d,p) basis set employing full geometry optimization and frontier orbital energies. The optimized geometric bond lengths and bond angles obtained by using DFT(B3LYP) showed the good agreement with the experimental data.
- Pan, Xian-Shuai,Sun, Na-Bo,Lei, Chao,He, Fang-Yue
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p. 350 - 354
(2014/07/08)
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- Acyl hydrazides: Potent antioxidants
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Twenty-eight acyl hydrazides (1-28) are subjected for nitric oxide scavenging activities and their structureactivity relationship (SAR) is established. Compounds 1-28 showed a varying degree of activity having IC 50 values in the range of 9.1 ± 6.5 - 231.1 μM. It was found that twenty-five (25) out of twenty-eight (28) compounds, showed an excellent nitric oxide scavenging activity. It was observed that the activity mainly depends on the substitution on acyl hyrazide moiety. 3-Propylpyrozole-5- carbohydrazide (27) was found to be the most active in the series with an IC50 value of 9.1 μM. Thus, compound 27 may serve as a lead compound for further development as potent antioxidant agent.
- Khan, Khalid Mohammed,Rani, Mubeen,Ambreen, Nida,Ejaz, Asma,Perveen, Shahnaz,Haider, Syed Moazzam,Choudhary, Mohammad Iqbal,Voelter, Wolfgang
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scheme or table
p. 135 - 139
(2012/07/28)
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- Combinatorial synthesis of 3,5-Dimethylene substituted 1,2,4-Triazoles
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Combinatorial cyclizations of imidates and hydrazides with methylene linked R groups, generated from the corresponding nitriles and carboxylic acids, respectively, provided a large library of 3,5-dimethylene substituted 1,2,4- trizoles. 2011 Bentham Science Publishers Ltd.
- Woodard, Scott S.,Jerome, Kevin D.
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experimental part
p. 132 - 137
(2012/04/18)
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- Development and assessment of green synthesis of hydrazides
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An expeditious, solvent free one pot method for the preparation of hydrazides from corresponding acids directly under microwave irradiation is developed. The method has been assessed using green chemistry measures and found superior to conventional method with higher E(environmental) factor, atom economy, atom efficiency, carbon efficiency, reaction mass efficiency.
- Saha, Ajoy,Kumar, Rajesh,Kumar, Rajendra,Devakumar
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experimental part
p. 526 - 531
(2010/10/03)
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- Keto-1,3,4-oxadiazoles as cathepsin K inhibitors
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We have prepared a series of cathepsin K inhibitors bearing the keto-1,3,4-oxadiazole warhead capable of forming a hemithioketal complex with the target enzyme. By modifying binding moieties at the P1, P2, and prime side positions of the inhibitors, we have achieved selectivity over cathepsins B, L, and S, and have achieved sub-nanomolar potency against cathepsin K. This series thus represents a promising chemotype that could be used in diseases implicated by imbalances in cathepsin K activity such as osteoporosis.
- Palmer, James T.,Hirschbein, Bernard L.,Cheung, Harry,McCarter, John,Janc, James W.,Yu, Z. Walter,Wesolowski, Gregg
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p. 2909 - 2914
(2008/09/21)
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- TRICYCLIC BENZAZEPINE DERIVATIVES AS SQUALENE SYNTHASE INHIBITORS USED FOR THE TREATMENT OF CARDIOVASCULAR DISEASES
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The invention relates to novel tricyclic benzazepine derivatives of formula (I), methods for the production thereof, the use thereof for treating and/or preventing diseases, and the use thereof for producing medicaments used for the treatment and/or prophylaxis of diseases, preferably cardiovascular diseases, particularly dyslipidemia, arteriosclerosis, restenosis, and ischemia.
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Page/Page column 31
(2008/06/13)
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- Synthesis and in vitro leishmanicidal activity of some hydrazides and their analogues
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Twenty-one hydrazides were synthesized by treating different esters with hydrazine hydrate. Substituted hydrazides were obtained by treating hydrazides with alkyl/aryl/acyl halides. Some of these compounds exhibit potential in vitro leishmanicidal activity. The structures of all the synthesized compounds were confirmed by spectroscopic analysis.
- Khan, Khalid Mohammad,Rasheed, Maimona,Ullah, Zia,Hayat, Safdar,Kaukab, Farhana,Choudhary, M. Iqbal,Ur-Rahman, Atta,Perveen, Shahnaz
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p. 1381 - 1387
(2007/10/03)
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- Thiazole compounds and methods of modulating signal transduction
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The present invention relates to thiazole containing compounds capable of inhibiting protein tyrosine phosphatase activity. The invention further relates to the use of such compounds to modulate or regulate signal transduction by inhibiting protein tyrosine phosphatase activity. Finally, the invention relates to the use of such compounds to treat various disease states including diabetes mellitus.
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