cas 15678-99-6, N-(TERT-BUTYL)-2-CHLOROACETAMIDE

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Templated C-C and C-N Bond Formation Facilitated by a Molybdenum(VI) Metal Center
Preparation of molybdenum dioxido complexes with novel iminophenolate ligands bearing pendant secondary amide functionalities led to unprecedented C-C and C-N coupling reactions of two α-iminoamides upon coordination. The diastereoselective cyclization to asymmetric imidazolidines occurs at the metal center in two consecutive steps via a monocoupled intermediate. A meaningful mechanism is proposed on the basis of full characterization of intermediate and final molybdenum-containing products by spectroscopic means and by single-crystal X-ray diffraction analyses. This process constitutes the first example of a diastereoselective self-cyclization of two α-iminoamides.
Zwettler, Niklas,Dupé, Antoine,Schachner, J?rg A.,Belaj, Ferdinand,M?sch-Zanetti, Nadia C.
p. 11969 - 11976
(2015)
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Neutral and cationic yttrium alkyl complexes with linked 1,4,7-triazacyclononane-amide monoanionic ancillary ligands: Synthesis and catalytic ethene polymerisation
Yttrium dialkyl complexes [N,N′-R2-tacn-N″-(CH2)2 NBut]-Y(CH2SiMe3)2 (R = Me, Pri; tacn = 1,4,7-triazacyclononane) were prepared; when activated with [PhNMe2H]-[B(C6F5)4] these complexes form cationic alkyl species that are active ethene polymerisation catalysts.
Bambirra,Van Leusen,Meetsma,Hessen,Teuben
p. 637 - 638
(2001)
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Synthesis and Structure–Activity Relationship of Thioacetamide-Triazoles against Escherichia coli
Infections due to Gram-negative bacteria are increasingly dangerous due to the spread of multi-drug resistant strains, emphasizing the urgent need for new antibiotics with alternative modes of action. We have previously identified a novel class of antibacterial agents, thioacetamide-triazoles, using an antifolate targeted screen and determined their mode of action which is dependent on activation by cysteine synthase A. Herein, we report a detailed examination of the anti-E. coli structure–activity relationship of the thioacetamide-triazoles. Analogs of the initial hit compounds were synthesized to study the contribution of the aryl, thioacetamide, and triazole sections. A clear structure–activity relationship was observed generating compounds with excellent inhibition values. Substitutions to the aryl ring were generally best tolerated, including the introduction of thiazole and pyridine heteroaryl systems. Substitutions to the central thioacetamide linker section were more nuanced; the introduction of a methyl branch to the thioacetamide linker substantially decreased antibacterial activity, but the isomeric propionamide and N-benzamide systems retained activity. Changes to the triazole portion of the molecule dramatically decreased the antibacterial activity, further indicating that 1,2,3-triazole is critical for potency. From these studies, we have identified new lead compounds with desirable in-vitro ADME properties and in-vivo pharmacokinetic properties.
Bulitta, Jürgen B.,Dharuman, Suresh,Lee, Richard E.,Reeve, Stephanie M.,Wallace, Miranda J.
supporting information

(2022/03/01)

METHODS OF USE FOR PYRIMIDINES AS FERROPORTIN INHIBITORS
The subject matter described herein is directed to ferroportin inhibitor compounds of Formula (I) and pharmaceutical salts thereof, methods of preparing the compounds, pharmaceutical compositions comprising the compounds, and methods of administering the compounds for prophylaxis and/or treatment of diseases caused by a lack of hepcidin or iron metabolism disorders, particularly iron overload states, such as thalassemia, sickle cell disease and hemochromatosis, and also kidney injuries.
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Paragraph 849-852

(2021/11/06)

Synthesis and Biological Evaluation of 1,2,4-Triazole Thioethers as Both Potential Virulence Factor Inhibitors against Plant Bacterial Diseases and Agricultural Antiviral Agents against Tobacco Mosaic Virus Infections
Targeting the virulence factors of phytopathogenic bacteria is an innovative strategy for alleviating or eliminating the pathogenicity and rapid outbreak of plant microbial diseases. Therefore, several types of 1,2,4-triazole thioethers bearing an amide l
Fang, Zi-Mian,Guo, Deng-Xuan,Ji, Jin,Liu, Li-Wei,Qi, Pu-Ying,Shao, Wu-Bin,Wang, Jin-Jing,Wang, Pei-Yi,Yang, Song,Zhou, Xiang
p. 15108 - 15122
(2021/12/27)

Design, Synthesis, and SAR Studies of Heteroarylpyrimidines and Heteroaryltriazines as CB2R Ligands
Herein we describe the design and synthesis of a new series of heteroarylpyrimidine/heteroaryltriazine derivatives on the basis of quinazoline-2,4(1H,3H)-diones as CB2R-selective ligands using a bioisosterism strategy. An acetamide group was explored to displace the enamine linker of the lead compound for the purpose of stereoisomerism elimination and hydrophilicity increase. As a result, some of the synthesized compounds showed high bioactivity and selectivity for CB2R in calcium mobilization assays, and four displayed CB2R agonist activity, with EC50 values below 30 nm. The compound exhibiting the highest agonist activity toward CB2R (EC50=7.53±3.15 nm) had a selectivity over CB1R of more than 1328-fold. Moreover, structure–activity relationship (SAR) studies indicated that the substituents on the nucleus play key roles in the functionality of a ligand, with one such example demonstrating CB2R antagonist activity. Additionally, molecular docking simulations were conducted with the aim of better understanding of these new derivatives in relation to the structural requirements for agonists/antagonists binding to CB2R.
Qian, Hai-Yan,Wang, Zhi-Long,Chen, Li-Li,Pan, You-Lu,Xie, Xiao-Yu,Xie, Xin,Chen, Jian-Zhong
supporting information
p. 2455 - 2463
(2018/11/23)

Development of Quinazoline/Pyrimidine-2,4(1H,3H)-diones as Agonists of Cannabinoid Receptor Type 2
Starting from a prototypical structure 1, we describe our efforts to design and obtain novel quinazoline/pyrimidine-2,4(1H,3H)-diones with high CB2 agonist potency and selectivity as well as improved physicochemical characteristics, mainly hydrophilicity. The most potent and selective CB2 agonists, 8 and 36, in this series were also endowed with lower logP values than that of GW842166X and lead compound 1. These derivatives appear to be promising lead compounds for the development of future CB2 agonists.
Qian, Hai-Yan,Wang, Zhi-Long,Pan, You-Lu,Chen, Li-Li,Xie, Xin,Chen, Jian-Zhong
supporting information
p. 678 - 681
(2017/06/13)

Carbamylmethyl Mercaptoacetate Thioether: A Novel Scaffold for the Development of L1 Metallo-β-lactamase Inhibitors
Given the clinical importance of metallo-β-lactamases (MβLs), a new scaffold, N-substituted carbamylmethyl mercaptoacetate thioether, was constructed. The obtained molecules 1-16 inhibited MβLs from all three subclasses, but preferentially L1 from subclass B3. Compound 9 with a p-carboxyphenyl substituent exhibited the broadest spectrum with at least 70% inhibition of enzymes from all subclasses at 100 μM, while compound 5 with a p-methylphenyl substituent was the most potent inhibitor of any individual enzyme, with 97% inhibition at 100 μM and an IC50 value of 0.41 μM against L1. Isothermal titration calorimetry assays corroborate findings from UV-vis spectrophotometric assays that the inhibition of L1 by 5 is dose-dependent. Docking studies suggest that the carboxyl group, the sulfide atom, and the carbonyl group of the carbamyl coordinate Zn2 in a chelating fashion. Using E. coli cells expressing L1, 6 and 8 were able to decrease cefazolin minimum inhibitory concentration 8-fold.
Chang, Ya-Nan,Xiang, Yang,Zhang, Yue-Juan,Wang, Wen-Ming,Chen, Cheng,Oelschlaeger, Peter,Yang, Ke-Wu
supporting information
p. 527 - 532
(2017/05/19)

1,3-dimethyl-7-substituted-quinazolinyl-2,4-diones, and synthesis method and application thereof
The invention discloses 1,3-dimethyl-7-substituted-quinazolinyl-2,4-diones. The structural general formula of the compounds is disclosed in the specification, wherein R1 is hydrogen or ethyl; and R2 is a benzene ring, benzene ring derivative, heterocyclic ring or aliphatic hydrocarbon. Part of compounds have favorable inhibiting activities for Candida albicans, Aspergillus flavus, Torula histolytica and Aspergillus fumigatus. The compounds have obvious inhibiting activities for chitin synthetase, have favorable antibacterial effects, and can be used for preparing drugs for anti-pathogenic microorganisms.
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Paragraph 0056; 0057; 0058; 0059; 0060; 0099; 0100

(2017/07/31)

TREATMENT OF INFECTIOUS DISEASES WITH GLUCOSE UPTAKE INHIBITORS
Provided are methods of treating infectious diseases in mammals comprising administering a compound that inhibits glucose uptake. Particular infectious diseases that may be treated include malaria, leishmaniasis, African trypanosomiasis, tuberculosis, HIV, HCMV or herpes virus. In a first aspect, the invention features a method of treating infectious diseases in a mammal, comprising administering to a mammalian subject in need thereof a therapeutically effective amount of a compound or prodrug thereof, or pharmaceutically acceptable salt or ester of said compound or prodrug, wherein the compound is an inhibitor of glucose uptake.
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Paragraph 0145; 0146

(2017/01/09)

GLUCOSE UPTAKE INHIBITORS
Provided hererin are compounds that modulate glucose uptake activityand are useful for treating cancer, autoimmune diseases, inflammation, infectious diseases, and metabolic diseases. In certain embodiments, the compounds modulate glucose uptake activity by modulating cellular components, including, but not limited to those related to glycolysis and known transporters/co-transporters of glucose such as GLUT1 and other GLUT family members/alternative hexose transporters. In certain embodiments, the compounds have the structure of formula I: Formula (I) wherein the variables have the values disclosed herein.
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Paragraph 0281-0282

(2017/01/09)

Heteroarylpyrimindinedione derivative and use thereof
The invention provides a heteroarylpyrimindinedione derivative and use thereof. The heteroarylpyrimindinedione derivative comprises a compound with a structure shown as general formula I, and a pharmaceutically acceptable salt or hydrate thereof. The derivative is obtained by chemical synthesis, and pharmacological experiments prove that the active ligand with cannabinoid type II receptor CB2 can be used for preparation of drugs for prevention and mitigation of CB2 receptor-mediated diseases, and the drug is cannabinoid CB2 receptor agonist's agonist, partial agonist, inverse agonist or antagonist. And the general structural formula I is shown as the specification.
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Paragraph 0099; 0100

(2017/04/03)

Quinazoline dione derivatives and preparation method and application thereof
The invention provides novel quinazoline dione derivatives and a preparation method and application thereof. The compounds include compounds with the structure shown in the general formula V in the description and pharmaceutically acceptable salts or hydrates thereof. The compounds are active ligands of novel cannabinoid II receptors (CB2) and can be used for preparing medicine for treating, preventing and relieving CB2 receptor-mediated diseases, wherein the medicine is an agonist or partial agonist or inverse agonist or antagonist of CB2 receptors.
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Paragraph 0101; 0102; 0103

(2017/07/19)

Design, synthesis and evaluation of novel quinazoline-2,4-dione derivatives as chitin synthase inhibitors and antifungal agents
A series of novel 1-methyl-3-substituted quinazoline-2,4-dione derivatives were designed, synthesized, and characterized by 1H NMR, 13C NMR and MS spectral data. Their inhibition against chitin synthase (CHS) and antifungal activities were evaluated in vitro. Results showed compounds 5b, 5c, 5e, 5f, 5j, 5k, 5l, and 5o had strong inhibitory potency against CHS. Compound 5c, which has the highest potency among these compounds, had a half-inhibition concentration (IC50) of 0.08 mmol/L, while polyoxin B as positive drug had IC50 of 0.18 mmol/L. These IC 50 values of compounds 5i, 5m, 5n, and 5s were greater than 0.75 mmol/L, which revealed that those compounds had weak inhibition activity against CHS. Moreover, most of these compounds exhibited moderate to excellent antifungal activities. In detail, to Candida albicans, the activities of compound 5g and 5k were 8-fold stronger than that of fluconazole and 4-fold stronger than that of polyoxin B; to Aspergillus flavus, the activities of 5g, 5l and 5o were16-fold stronger than that of fluconazole and 8-fold stronger than that of polyoxin B; to Cryptococcus neoformans, the minimum-inhibition- concentration (MIC) values of compounds 5c, 5d, 5e and 5l were comparable to those of fluconazole and polyoxin B. The antifungal activities of these compounds were positively correlated to their IC50 values against CHS. Furthermore, these compounds had negligible actions to bacteria. Therefore, these compounds were promising selective antifungal agents.
Ji, Qinggang,Yang, Dan,Wang, Xin,Chen, Chunyan,Deng, Qiao,Ge, Zhiqiang,Yuan, Lvjiang,Yang, Xiaolan,Liao, Fei
p. 3405 - 3413
(2014/06/23)

Complexes of selected late period lanthanide(III) cations with 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid amide (DOTAM)-alkyl ligands-A new platform for the development of paramagnetic chemical exchange saturation transfer (PARACEST) magnetic resonance imaging (MRI) contrast agents
A series of 18 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid amide (DOTAM)-alkyl derived complexes with selected late lanthanide(III) cations (Dy3+, Tb3+, and Tm3+) has been synthesized; their magnetic properties have been evaluated and compared to those derived from DOTAM. Peralkylation of cyclen with corresponding N-iodoacetyl amines was utilized as the key step in the synthesis. Chemical exchange saturation transfer (CEST) spectra of the complexes have been acquired at 37 C, revealing that Tm3+-derived DOTAM-alkyl complexes possess the most favorable properties as potential paramagnetic chemical exchange saturation transfer (PARACEST) magnetic resonance imaging (MRI) contrast agents.
Elmehriki, Adam A.H.,Milne, Mark,Suchy, Mojmir,Bartha, Robert,Hudson, Robert H.E.
p. 211 - 219
(2013/05/22)

KINASE INHIBITORS
Methods of inhibiting kinases using kinase inhibitors having olefin moieties are disclosed.
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Paragraph 0453; 0454

(2013/03/26)

A formal method for the de-N,N-dialkylation of Sommelet-Hauser rearrangement products
Selective amine de-alkylation enables the conversion of Sommelet-Hauser rearrangement products into 2-aryl-2-bromoacetic acid derivatives. These compounds are valuable synthetic intermediates in the synthesis of α-aryl-α-amino or α-aryl-β-amino acid deriv
Tayama, Eiji,Sato, Ryota,Takedachi, Keisuke,Iwamoto, Hajime,Hasegawa, Eietsu
supporting information; experimental part
p. 4710 - 4718
(2012/07/28)

OXADIAZOLE INHIBITORS OF LEUKOTRIENE PRODUCTION
The present invention relates to compounds of formula (I) and pharmaceutically acceptable salts thereof, wherein R1-R5 are as defined herein. The invention also relates to pharmaceutical compositions comprising these compounds, metho
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Page/Page column 92-93

(2012/04/10)

Amberlyst-15 as a recyclable heterogeneous catalyst for synthesis of N-tert-butylamides via Ritter-type reaction
Highly efficient method for the preparation of N-tert-butylamides by reaction of nitriles with tert-butylacetate is described using Amberlyst-15 as a recyclable heterogeneous catalyst. Selective amidation of benzonitrile in the presence of acetonitrile was also achieved.
Mokhtary, Masoud,Goodarzi, Gholamreza
experimental part
p. 293 - 296
(2012/05/07)

Synthesis of 2H-1,4-benzoxazin-3(4H)-ones via smiles rearrangement
An efficient synthetic route for novel 2H-1,4-benzoxazin-3(4H)-ones via smiles rearrangement is developed. Reaction of primary amine and chloroacetyl chloride gave 2-chloroacetamide, which reacted with 2-chlorophenol, followed by Smiles rearrangement to o
Zhou, Jia-Zhou,Li, Zhu-Bo,Yang, Hao,He, Xiao-Yan,Wang, Li-Ying,Tian, Xiao,Lv, Ting-Ting,Zuo, Hua
experimental part
p. 2947 - 2950
(2012/01/05)

3-Fluoro-Piperidine T-Type Calcium Channel Antagonists
The present invention is directed to 3-fluoro-piperidine compounds which are antagonists of T-type calcium channels, and which are useful in the treatment or prevention of neurological and psychiatric disorders and diseases in which T-type calcium channel
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Page/Page column 12-13

(2010/09/07)

Modulating the development of E. coli biofilms with 2-aminoimidazoles
The synthesis of a 20 member 2-aminoimidazole/triazole pilot library is reported. Each member of the library was screened for its ability to inhibit or promote biofilm development of either Escherichia coli and Acinetobacter baumannii. From this screen, E. coli-selective 2-aminoimidazoles were discovered, with the best inhibitor inhibiting biofilm development with an IC50 of 13 μM. The most potent promoter of E. coli biofilm formation promoted biofilm development by 321% at 400 μM.
Reed, Catherine S.,Huigens III, Robert W.,Rogers, Steven A.,Melander, Christian
supporting information; experimental part
p. 6310 - 6312
(2010/11/18)

Safe and efficient ritter reactions in flow
Efficient mixing, temperature control and small environmental exposures allow reactions carried out in microfluidic de-vices to perform superior to their batch-type counterparts in conventional flasks. The Ritter reaction has been optimised for flow conditions leading to short reaction times and higher yields and also is more feasible with regards to safety, productivity and tolerance towards substrate functionalities.
Brandt, Johan C.,Elmore, Simon C.,Robinson, Richard I.,Wirth, Thomas
experimental part
p. 3099 - 3103
(2011/02/25)

BICYCLIC PYRIMIDINE DERIVATIVES AS CALCIUM CHANNEL BLOCKERS
Methods and compounds effective in ameliorating conditions characterized by unwanted calcium channel activity, particularly unwanted T-type calcium channel activity are disclosed. Specifically, a series of compounds containing thienopyrimidine or oxoquinazoline derivatives are disclosed of the general formula (1) or formula (2) where X is a linker and Y is an aromatic moiety or N(R5)(R6).
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(2008/12/08)

3-FLUORO-PIPERIDINE T-TYPE CALCIUM CHANNEL ANTAGONISTS
The present invention is directed to 3-fluoro-piperidine compounds which are antagonists of T-type calcium channels, and which are useful in the treatment or prevention of neurological and psychiatric disorders and diseases in which T-type calcium channel
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Page/Page column 25; 26

(2008/06/13)

4-FLUORO-PIPERIDINE T-TYPE CALCIUM CHANNEL ANTAGONISTS
The present invention is directed to 4-fluoro-piperidine compounds which are antagonists of T-type calcium channels, and which are useful in the treatment or prevention of neurological and psychiatric disorders and diseases in which T-type calcium channel
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Page/Page column 28-29

(2010/11/25)

Design and synthesis of heteroditopic aza-thioether macrocycles for metal extraction
A series of pendant arm aza-thioether macrocycles containing hydrogen-bonding amide functionalities have been synthesised and the single crystal X-ray structures of [12]aneS3N-CONHCOPh, [12]aneS 3N-CSNHCOPh, [12]aneS2ON-CO
Glenny, Mark W.,Lacombe, Marie,Love, Jason B.,Blake, Alexander J.,Lindoy, Leonard F.,Luckay, Robert C.,Gloe, Karsten,Antonioli, Bianca,Wilson, Claire,Schroeder, Martin
p. 1755 - 1767
(2008/02/05)

Cationic group-3 catalyst system
A cationic Group 3 or Lanthanide metal complex for coordination polymerization of olefins is disclosed. The precursor metal complex is stabilized by an anionic multidentate ancillary ligand and two monoanionic ligands. The ancillary ligand and the transition metal form a metallocycle having at least five primary atoms, counting any π-bound cyclopentadienyl group in the metallocycle as two primary atoms. Olefin polymerization is exemplified.
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(2008/06/13)

Reaction of different α-sulfonyl acetamides with methyl acrylate
The base-induced tandem-coupling/cyclization reactions of various α-sulfonyl acetamide derivatives A with methyl acrylate differentiated between two different pathways to form α-sulfonyl analogs of glutarimides B and 2-hydroxycyclohexenecarboxylic acid derivatives C in different ratios. The reaction of α-sulfonyl acetamide dianion with methyl acrylate depended on three factors: the stability of the dianion, concentration of methyl acrylate and the structure of sufonyl and amide substituents. By changing the reaction conditions, we efficiently controlled the cycloaddition reaction to synthesize the desired product, each of which has potential biological activities. A ring closure mechanism is proposed for the reactions.
Chang, Meng-Yang,Chen, Shui-Tein,Chang, Nein-Chen
p. 5075 - 5080
(2007/10/03)

Facile conversion of alcohols into N-substituted amides by magnesium hydrogensulfate under heterogeneous conditions
Different classes of alcohols react efficiently with nitriles in the presence of magnesium hydrogensulfate, Mg(HSO4)2, to produce amides in high yields.
Salehi,Khodaei,Zolfigol,Keyvan
p. 1947 - 1951
(2007/10/03)

Fe3+-montmorillonite K10: An efficient catalyst for selective amidation of alcohols with nitriles under non-aqueous condition
An efficient method for preparation of secondary amides by reaction of alcohols with nitriles is described using a catalytic amount of Fe3+- montmorillonite K10.
Lakouraj,Movassagh,Fasihi
p. 821 - 827
(2007/10/03)

Rare earth exchanged HY zeolite, an efficient catalyst for the synthesis of N-monosubstituted amides
The use of rare earth exchanged HY (RE HY) zeolite catalyst for the synthesis of N-monosubstituted amides 3a-g starting from alcohols 1 and nitriles 2 in good yields is described
Deshmukh, A. R. A. S.,Gumaste, V. K.,Bhawal, B. M.
p. 369 - 371
(2007/10/03)

5-Phenyl-3-ureidobenzazepin-2-ones as cholecystokinin-B receptor antagonists
A series of 5-phenyl-3-ureidobenzazepin-2-one cholecystokinin-B (CCK-B) receptor antagonists was synthesized using Beckmann ring expansion of a suitable 4-phenyl-1-tetralone as a key step. Structure-activity relationship studies revealed the importance of
Lowe III,Hageman,Drozda,McLean,Bryce,Crawford,Zorn,Morrone,Bordner
p. 3789 - 3811
(2007/10/02)

Lithium Bromide/Triethylamine Induced Cycloaddition of N-Alkylidene 2-Amino Esters and Amides to Electron-Deficient Olefins with High Regio- and Stereoselectivity
The imines of 2-amino esters and amides derived from glycine, alanine, and valine are deprotonated by the action of a lithium halide and triethylamine (or DBU).The resulting anionic intermediates undergo highly regio- and stereoselective cycloadditions with a variety of olefins activated by carbonyl-type substituents to produce stereochemically defined derivatives of proline esters or amides.The scope and limitations of this novel cycloaddition are discussed.
Tsuge, Otohiko,Kanemasa, Shuji,Yoshioka, Manabu
p. 1384 - 1391
(2007/10/02)

Synthese d'analogues tetrazoles de l'acide phosphonoacetique
Several routes to 5-(phosphonomethyl)-1(H)-tetrazole, a new antiviral agent, have been investigated.
Yaouanc,Sturtz,Kraus,Chastel,Colin
p. 2689 - 2692
(2007/10/02)