- Synthesis of a New Phorbazole and Its Derivatives
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Phorbazoles are chlorinated marine alkaloids containing pyrrole, oxazole and phenol ring units, and differ in the number and positions of chlorine atoms. They are isolated from sea sponges and nudibranchs. In this work, a convenient synthetic method leading to a new phorbazole and its derivatives is developed. This synthesis of synthetic phorbazole G and its derivatives is achieved in seven steps in good overall yields of 26-52%. It involves formation of the pyrrole-oxazole skeleton followed by chlorination. The pyrrole-oxazole skeleton is synthesized from pyrrole and substituted acetophenones, and the key step involves cyclodehydration of amide intermediates to give protected oxazoles, followed by hydrolysis.
- Louglin, Wendy A.,Muderawan, I Wayan,Young, David J.
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- Discovery of Imidazopyridines as Potent Inhibitors of Indoleamine 2,3-Dioxygenase 1 for Cancer Immunotherapy
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Indoleamine 2,3-dioxygenase 1 (IDO1) has been identified as a target for small-molecule immunotherapy for the treatment of a variety of cancers including renal cell carcinoma and metastatic melanoma. This work focuses on the identification of IDO1 inhibitors containing replacements or isosteres for the amide found in BMS-986205, an amide-containing, IDO1-selective inhibitor currently in phase III clinical trials. Detailed subsequently are efforts to identify a structurally differentiated IDO1 inhibitor via the pursuit of a variety of heterocyclic isosteres, leading to the discovery of highly potent, imidazopyridine-containing IDO1 inhibitors.
- Zhang, Liping,Cherney, Emily C.,Zhu, Xiao,Lin, Tai-An,Gullo-Brown, Johnni,Maley, Derrick,Johnston-Allegretto, Kathy,Kopcho, Lisa,Fereshteh, Mark,Huang, Christine,Li, Xin,Traeger, Sarah C.,Dhar, Gopal,Anandam, Aravind,Mahankali, Sandeep,Padmanabhan, Shweta,Rajanna, Prabhakar,Murali, Venkata,Mariappan, Thanga,Borzilleri, Robert,Vite, Gregory,Hunt, John T.,Balog, Aaron
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supporting information
p. 494 - 501
(2021/04/06)
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- The reaction of prop-2-ynylsulfonium salts and sulfonyl-protected β-amino ketones to epoxide-fused 2-methylenepyrrolidines and S-containing pyrroles
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A novel divergent domino annulation reaction of prop-2-ynylsulfonium salts with sulfonyl-protected β-amino ketones has been developed, affording various epoxide-fused 2-methylenepyrrolidines and S-containing pyrroles in moderate to excellent yields. Prop-2-ynylsulfonium salts act as C2synthons in the reactions providing a promising epoxide-fused skeleton in a single operation with readily accessible starting materials.
- Jia, Tingting,Zeng, Gongruixue,Zhang, Chong,Zeng, Linghui,Zheng, Wenya,Li, Siyao,Wu, Keyi,Shao, Jiaan,Zhang, Jiankang,Zhu, Huajian
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supporting information
p. 2657 - 2660
(2021/03/16)
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- Synthesis of 2-Amino Substituted Oxazoles from α-Amino Ketones and Isothiocyanates via Sequential Addition and I2-Mediated Desulfurative Cyclization
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Oxazol-2-amines were synthesized by annulation of α-amino ketones and isothiocyanates. This sequential synthetic process involves addition of α-amino ketones to isothiocyanates and I2-promoted desulfurative cyclization omitting isolation of the less stable thiourea intermediates. It is transition metal-free and operationally simple, providing access to a variety of 2-amino substituted oxazole derivatives under mild reaction conditions. (Figure presented.).
- Chang, Junbiao,Yu, Wenquan,Zhang, Shuangshuang,Zhao, Qiongli,Zhao, Yifei
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supporting information
(2020/04/29)
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- Combating fluconazole-resistant fungi with novel β-azole-phenylacetone derivatives
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A series of β-azole-phenylacetone derivatives with novel structures were designed and synthesized to combat the increasing incidence of susceptible fungal infections and drug-resistant fungal infections. The antifungal activity of the synthesized compounds was assessed against five susceptible strains and five fluconazole-resistant strains. Antifungal activity tests showed that most of the compounds exhibited excellent antifungal activities against five pathogenic strains with MIC values in the range of 0.03–1 μg/mL. Compounds with R1 = 3-F substituted and 15o and 15ae exhibited moderate antifungal activities against fluconazole-resistant strains 17# and CaR with MIC values in the range of 1–8 μg/mL. Compounds with R1 = H or 2-F (such as 15a, 15o, 15p) displayed moderate to good antifungal activity against fluconazole-resistant strains 632, 901 and 904 with MIC values in the range of 0.125–4 μg/mL. Notably, 15o and 15ae exhibited antifungal activity against five susceptible strains and five fluconazole-resistant strains. Preliminary mechanistic studies showed that the potent antifungal activity of compound 15ae stemmed from inhibition of C. albicans CYP51. Compounds 15o, 15z and 15ae were nearly nontoxic to mammalian A549 cells.
- Zhao, Liyu,Sun, Nannan,Tian, Linfeng,Sun, Yin,Chen, Yixuan,Wang, Xinran,Zhao, Shizhen,Su, Xin,Zhao, Dongmei,Cheng, Maosheng
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- AMINOPYRIDINE DERIVATIVES AS TAM FAMILY KINASE INHIBITORS
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Provided herein are aminopyridine derivatives and pharmaceutical compositions that are useful as TAM family kinase inhibitors.
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Page/Page column 58
(2015/06/11)
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- Palladium-catalysed carbonylative α-arylation of nitromethane
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A simple and mild Pd-catalysed carbonylative α-arylation of nitromethane has been realised providing access to α-nitro aryl ketones from an array of aryl and heteroaryl iodides. The methodology requires only a mild base and uses the convenient solid CO re
- Lian, Zhong,Friis, Stig D.,Skrydstrup, Troels
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supporting information
p. 3600 - 3603
(2015/04/13)
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- Rearrangement of N-tert-butanesulfinyl α-halo imines with alkoxides to N-tert-butanesulfinyl 2-amino acetals as precursors of N-protected and N-unprotected α-amino carbonyl compounds
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Reaction of N-tert-butanesulfinyl α-halo imines with alkoxides afforded new N-tert-butanesulfinyl 2-amino acetals in good to excellent yield. These N-tert-butanesulfinyl 2-amino acetals are convenient precursors for the TMSOTf-promoted synthesis of the co
- Colpaert, Filip,Mangelinckx, Sven,Denolf, Bram,De Kimpe, Norbert
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experimental part
p. 6023 - 6032
(2012/10/08)
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- Compositions and Methods for Controlling Nematodes
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Compositions and processes for controlling nematodes are described herein, e.g., nematodes that infest plants or animals. The compounds include oxazoles, oxadiazoles and thiadiazoles.
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Page/Page column 34
(2010/08/22)
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- OXADIAZOLE- AND OXAZOLE-SUBSTITUTED BENZIMIDAZOLE- AND INDOLE-DERIVATIVES AS DGAT1 INHIBITORS
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The present invention provides oxadiazolyl- substituted benzimidazole- and idole-derivates that are useful for treating conditions or disorders associated with DGAT1 activity in animals, particularly humans.
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Page/Page column 75
(2009/05/29)
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- MODULATION OF PROTEIN TRAFFICKING
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Compounds and compositions are provided for treatment or amelioration of one or more disorders characterized by defects in protein trafficking. A method of treating a disorder characterized by impaired protein trafficking includes administering to a subject or contacting a cell with a compound of Formula I: [formula here] or pharmaceutically acceptable salts or derivatives thereof.
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Page/Page column 209-210
(2009/06/27)
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- P70 S6 KINASE INHIBITORS
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The present invention provides p70 S6 kinase inhibitors of the formula: pharmaceutical formulations comprising them, and methods for their use.
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Page/Page column 16-17
(2009/01/20)
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- COMPOUNDS WITH ACTIVITY AT RETINOIC ACID RECEPTORS
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Disclosed herein is a compound of Formula (I) and pharmaceutical composition comprising the same. Also disclosed herein are methods of treating, or alleviating the symptoms of, a disease comprising administering to a subject in need thereof a therapeutically effective amount of a compound of Formula (I). The disease may be selected from the group consisting of cancer, hyperproliferative disorder, inflammatory disorder, neurological disorder, neurodegenerative disorder, eye disorder, eye condition, depression, pulmonary disorders/conditions, dermatological disorders/conditions, and infertility.
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Page/Page column 42-43
(2008/12/05)
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- Synthesis and biological evaluation of imidazol-2-one derivatives as potential antitumor agents
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A new series of aryl substituted imidazol-2-one derivatives structurally related to combretastatin A-4 (CA-4) were synthesized and evaluated for their cytotoxic activities in vitro against various human cancer cell lines including MDR cell line. The cytotoxic effects of compounds 7b and 7i proved to be similar to or greater than that of docetaxel. The highly active compound 7b also exhibited excellent inhibitory activity on tumor growth in vivo.
- Xue, Na,Yang, Xiaochun,Wu, Rui,Chen, Jing,He, Qiaojun,Yang, Bo,Lu, Xiuyang,Hu, Yongzhou
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p. 2550 - 2557
(2008/09/21)
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- Synthesis and anticonvulsant activity of some new 4-aryl-4-imidazoline-2-one derivatives
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In this study, some new 4-aryl-4-imidazoline-2-one deriratives have been prepared by the reaction of potassium cyanate with some aminoethanone hydrochlorides. The structure of these compounds have been confirmed by UV, IR, 1H-NMR and elementary analysis. Their anticonvulsant activities were determined by maximal electroshock (MTS) and subcutaneous metrazol (scMet) tests according to the ADD (Antiepileptic Drug Development) programme Phase I. Neurotoxicity of the compounds was evaluated by rotarod test. While 2 of the compounds showed protection against ScMet induced seizures at 30 and 300 mg/kg dose levels, 3 of the compounds showed neurotoxicity.
- Calis,Dalkara,Ertan
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p. 592 - 594
(2007/10/02)
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- A Convenient Synthesis of Aminomethyl Ketones (α-Amino Ketones)
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Several N,N-diformylaminomethyl ketones 3 were prepared by treating the respective bromomethylketone 1 with sodium diformylamide in acetonitrile at room temperature.This reaction produced from N-formylaminomethyl ketones 4 when ethanol was used as the solvent.One of the formyl groups of N,N-difomylaminomethyl ketones was selectively removed by using a catalytic amount of sodium or potassium hydroxide in alcohol to the corresponding N-formylaminomethyl ketones 4.The formyl groups of both N,N-diformyl- and N-formylaminomethyl ketones could be easily removed by either5percent hydrochloric acid in ethanol or 6N hydrochloric acid to give the corresponding aminomethyl ketone hydrochlorides 5.These reactions are general and give high yield of the products.
- Yinglin, Han,Hongwen, Hu
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p. 615 - 618
(2007/10/02)
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- Substituted quinolinecarboxylic acids
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Substituted quinolinecarboxylic acids useful in the treatment of arthritis by inhibiting the progressive joint deterioration characteristic of arthritic disease and for inducing immunosuppression are disclosed. Methods of synthesis and use of the novel compounds are also disclosed.
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- Synthesis of 4-oxopyrrolopyrimidine-3-carboxylic acid derivatives as potential antimicrobial agents
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A route for the synthesis of various derivatives of 4-oxopyrrolopyrimidine-3-carboxylic acid from 2-amino-3-cyano-4,5-dimethylpyrrole and 2-amino-3-cyano-4-arylpyrroles is described.
- Bayomi, Said M.,Al-Obaid, Abdul Rahman M.,Jado, Ahmad I.,Loutfy, Essam A.
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p. 814 - 816
(2007/10/02)
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- A CONVENIENT PREPARATION OF AMINOMETHYL ARYL KETONES AND THEIR DERIVATIVES
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A convenient preparation of N-phenacyl diformamides, N-phenacyl formamides and aminomethyl aryl ketone hydrochlorides from aryl bromomethyl ketones and sodium diformylamide was described.
- Ying-lin, Han,Hong-ven, Hu
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p. 5285 - 5286
(2007/10/02)
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- SYNTHESIS OF α-AMINO KETONE HYDROCHLORIDES VIA CHEMOSELECTIVE HYDROGENATION OF α-NITRO KETONES
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Chemoselective hydrogenation of various α-nitro ketones was accomplished with 5percent Pt sulfide on carbon as a catalyst to afford α-amino ketone hydrochlorides in good yields.
- Tamura, Rui,Oda, Daihei,Kurokawa, Hiroshi
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p. 5759 - 5762
(2007/10/02)
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- New Anticancer Agents: Synthesis of 1,2-Dihydropyridopyrizines (1-Deaza-7,8-dihydropteridines)
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Reaction of α-aminoacetophenone oximes (2) with ethyl 6-amino-4-chloro-5-nitropyridine-2-carbamate (1) gave ethyl 6-amino-5-nitro-4-pyridine-2-carbamate oximes (3), which were hydrolyzed under acidic conditions to give the corresponding ketones (4).Related pyridines substituted with keto side chain were prepared from 1 and 1,3-diaminopropanone oximes and by oxidation of the side-chain hydroxy group of ethyl 6-amino-4-amino>-5-nitropyridine-7-carbamates (6).Catalytic hydrogenation of the nitro group of 4 over Raney nickel in a large volume of ethanol gave the 1-deaza-7,8-dihydropteridines (7).Several of the oximes 3 were successfully hydrogenated to give 7 directly.The resulting 1-deaza-7,8-dihydropteridines showed potent cytotoxicity against cultured L1210 cells and significant anticancer activity against lymphocytic leukemia P-388 in mice.THese biological activities are attributed to the accumulation of cells at mitosis.
- Temple, Carroll,Wheeler, Glynn P.,Elliott, Robert D.,Rose, Jerry D.,Kussner, Conrad L.,et al.
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p. 1045 - 1050
(2007/10/02)
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- 1-[[[5-(Substituted phenyl)-2-oxazolyl]methylene]amino]-2,4-imidazolidinediones
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A series of 1-[[[5-(substituted phenyl-2-oxazolyl]methylene]amino]-2,4-imidazolidinediones are useful as muscle relaxants.
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