- Orientation effects on C2(5)-C2?(5?) linked bioxazole isomers synthesized via regioselective and sequential C[sbnd]H arylation
-
Bis(4-fluorophenyl) substituted oxazole (2,5-Oxz) and C2(5)-C2?(5?) linked bioxazole isomers (C2-C2?_BOxz, C2-C5?_BOxz and C5-C5?_BOxz) were concisely synthesized via palladium-catalyzed regioselective and sequential C[sbnd]H arylation in 1–3 reaction steps along with 20%–83% of total yields from oxazole and 4-bromofluorobenzene. The linking orientation plays a key role in the packing geometry and photophysical properties of C2-C2'_BOxz, C2-C5'_BOxz and C5-C5'_BOxz. These bioxazole isomers in solid state showed significant differences in photoluminescence quantum yields (PLQY) (0.33, 0.25 and 0.04, respectively), delayed fluorescence properties and powder X-ray diffraction (PXRD) patterns, suggesting the divergence in intermolecular interactions. The theoretically calculated gradient isosurfaces and complexation energies indicate the existence of intense π-π interactions between molecular layers, which are in good agreement with the variation trend of optical properties.
- Guo, Qiang,Tao, Li,Liu, Chuanqi,Zhao, Xiaoyun,Wan, Danyang,Zhang, Jincheng,Ai, Jianping,Li, Jie
-
-
Read Online
- HETEROARYL SUBSTITUTED SPIROPIPERIDINYL DERIVATIVES AND PHARMACEUTICAL USES THEREOF
-
The present invention provides a compound of formula (I) or a pharmaceutically acceptable salt thereof; (I) wherein R1 R2, R4 and X1 are defeined herein, a method for manufacturing the compounds of the invention, and its therapeutic uses. The present invention further provides a combination of pharmacologically active agents and a pharmaceutical composition.
- -
-
Page/Page column 109
(2022/02/22)
-
- INHIBITOR COMPOUNDS
-
The disclosure relates to heterocyclic compounds and methods for their preparation. The disclosure provides compounds that may have beneficial therapeutic activity in the treatment of a disease or condition mediated by excessive or otherwise undesirable Des1 and/or fibrotic activity.
- -
-
Page/Page column 63; 158-159
(2021/01/29)
-
- Design, synthesis and biological evaluation of imidazole and oxazole fragments as HIV-1 integrase-LEDGF/p75 disruptors and inhibitors of microbial pathogens
-
We describe here the synthesis of libraries of novel 1-subtituted-5-aryl-1H-imidazole, 5-aryl-4-tosyl-4,5-dihydro-1,3-oxazole and 5-aryl-1,3-oxazole fragments via microwave (MW)-assisted cycloaddition of para-toluenesulfonylmethyl isocyanide (TosMIC) to imines and aldehydes. The compounds obtained were biologically evaluated in an AlphaScreen HIV-1 IN-LEDGF/p75 inhibition assay with six imidazole-based compounds (16c, 16f, 17c, 17f, 20a and 20d) displaying more than 50% inhibition at 10 μM, with IC50 values ranging from 7.0 to 30.4 μM. Additionally the hypothesis model developed predicts all active scaffolds except 20d to occupy similar areas as the N-heterocyclic (A) moiety and two aromatic rings (B and C) of previously identified inhibitor 5. These results indicate that the identified compounds represent a viable starting point for their use as templates in the design of next generation inhibitors targeting the HIV-1 IN and LEDGF/p75 protein-protein interaction. In addition, the in vitro antimicrobial properties of these fragments were tested by minimum inhibitory concentration (MIC) assays showing that compound 16f exhibited a MIC value of 15.6 μg/ml against S. aureus, while 17f displayed a similar MIC value against B. cereus, suggesting that these compounds could be further developed to specifically target those microbial pathogens.
- Rashamuse, Thompho J.,Harrison, Angela T.,Mosebi, Salerwe,van Vuuren, Sandy,Coyanis, E. Mabel,Bode, Moira L.
-
-
- MCR scaffolds get hotter with 18F-Labeling
-
Imaging techniques, such as positron emission tomography (PET), represent great progress in the clinical development of drugs and diagnostics. However, the efficient and timely synthesis of appropriately labeled compounds is a largely unsolved problem. Nu
- Zarganes-Tzitzikas, Tryfon,Clemente, Gon?alo S.,Elsinga, Philip H.,D?mling, Alexander
-
-
- Reaction Conditions for the Regiodivergent Direct Arylations at C2- or C5-Positions of Oxazoles using Phosphine-Free Palladium Catalysts
-
Two sets of reaction conditions for the regiodivergent C2- or C5- direct arylations of oxazole are reported. In both cases, phosphine-free catalysts and inexpensive bases were employed allowing the access to the arylated oxazoles in moderate to high yields. Using Pd(OAc)2/KOAc as catalyst and base, regioselective C5-arylations were observed; whereas, using Pd(acac)2/Cs2CO3 system, the arylation occurred at the C2-position of oxazole. The higher reactivity of C5-H bond of oxazole as compared to the C2-H bond in the presence of Pd(OAc)2/KOAc system is consistent with a concerted metalation deprotonation mechanism; whereas the C2-arylation likely occurs via a simple base deprotonation of the oxazole C2-position. Then, from these C2- or C5-arylated oxazoles, a second palladium-catalyzed direct C?H bond arylation affords 2,5-diaryloxazoles with two different aryl groups. We also applied these sequential arylations to the straightforward synthesis of 2-arylphenanthro[9,10-d]oxazoles via three C?H bond functionalization steps. The Ru-catalyzed C?H arylation of the aryl unit of 2-aryloxazoles is also described. (Figure presented.).
- Shi, Xinzhe,Soulé, Jean-Fran?ois,Doucet, Henri
-
p. 4748 - 4760
(2019/09/12)
-
- Improvement of the Van Leusen reaction in the presence of β-cyclodextrin: A green and efficient synthesis of oxazoles in water
-
An efficient approach for the synthesis of oxazoles through the Van Leusen reaction in the presence of β-cyclodextrin is described. In aqueous medium using β-cyclodextrin as a supramolecular catalyst, tosylmethyl isocyanide was deprotonated by triethylami
- Rahimzadeh, Golnaz,Kianmehr, Ebrahim,Mahdavi, Mohammad
-
p. 923 - 926
(2017/12/18)
-
- A One-Pot Tandem Approach for the Synthesis of 5-(Het)aryloxazoles from Substituted (Het)aryl Methyl Alcohols and Benzyl Bromides
-
A new modified van Leusen strategy has been developed for the synthesis of biologically significant 5-substituted oxazoles by the reaction of (het)aryl methyl alcohols or benzyl bromides as precursors with tosylmethylisocyanide (TosMIC) under basic conditions. This method is efficient, takes place under mild reaction conditions, and is tolerant of various functional groups with high yield.
- Vinay Kumar, Koravangala S.,Swaroop, Toreshettahally R.,Rajeev, Narasimhamurthy,Vinayaka, Ajjampura C.,Lingaraju, Gejjalagere S.,Rangappa, Kanchugarakoppal S.,Sadashiva, Maralinganadoddi P.
-
supporting information
p. 1363 - 1366
(2016/06/01)
-
- Tandem cycloaddition-decarboxylation of α-keto acid and isocyanide under oxidant-free conditions towards monosubstituted oxazoles
-
An efficient method, tandem [3 + 2] cycloaddition-decarboxylation of α-keto acid and isocyanide promoted by copper salt, has been developed. Under oxidant-free conditions, a series monosubstituted oxazoles have been constructed. Different from the traditional application of α-oxo acids as acyl surrogates, the elegant approach herein ingeniously avoids consuming excess oxidants.
- Zhang, Ling-Juan,Xu, Mei-Chen,Liu, Jie,Zhang, Xian-Ming
-
p. 73450 - 73453
(2016/08/18)
-
- Nickel-catalyzed decarboxylative acylation of heteroarenes by sp 2 C-H functionalization
-
Nickel-catalyzed ligand-free decarboxylative cross-coupling of azole derivatives with α-oxoglyoxylic acids has been developed. This work represents the first example of decarboxylative cross-coupling reactions, in a C-H bond functionalization manner, thro
- Yang, Ke,Zhang, Cheng,Wang, Peng,Zhang, Yan,Ge, Haibo
-
supporting information
p. 7241 - 7244
(2014/06/23)
-
- Nickel-catalyzed decarboxylative arylation of heteroarenes through sp2 C-H functionalization
-
The direct decarboxylative arylation of hetereoarenes with benzoic acids through a nickel-catalyzed sp2 C-H functionalization process was developed. This process provides the first examples of decarboxylative cross-coupling reactions with aroma
- Yang, Ke,Wang, Peng,Zhang, Cheng,Kadi, Adnan A.,Fun, Hoong-Kun,Zhang, Yan,Lu, Hongjian
-
supporting information
p. 7586 - 7589
(2015/04/22)
-
- 3,8-DIAZA-BICYCLO[4.2.0]OCT-3-YL AMIDES
-
The present invention relates to 3,8-diaza-bicyclo[4.2.0]oct-3-yl amide derivatives of formula (I), wherein the relative configuration of the diazabicyclooctane moiety is cis; and wherein Ar1, and Ar2 are as described in the description, to their preparation, to pharmaceutically acceptable salts thereof, and to their use as pharmaceuticals, to pharmaceutical compositions containing one or more compounds of formula (I), and especially to their use as orexin receptor antagonists.
- -
-
Page/Page column 64
(2012/07/13)
-
- 3,8-DIAZA-BICYCLO[4.2.0]OCT-8-YL AMIDES
-
The present invention relates to 3,8-diaza-bicyclo[4.2.0]oct-8-yl amide derivatives of formula (I) Formula (I) wherein the relative configuration of the diazabicyclooctane moiety is cis; and wherein Ar1, and Ar 2 are as described in the description, to their preparation, to pharmaceutically acceptable salts thereof, and to their use as pharmaceuticals, to pharmaceutical compositions containing one or more compounds of formula (I), and especially to their use as orexin receptor antagonists.
- -
-
Page/Page column 56
(2012/07/13)
-
- ARYLOXAZOLE, ARYLOXADIAZOLE AND BENZIMIDAZOLE DERIVATIVES
-
This invention relates to compounds of the formula wherein X is O or NR8, Y is CR7 or N, and R1 to R8 are as defined in the specification, and pharmaceutically acceptable salts thereof. The invention further relates to pharmaceutical compositions containing such compounds, to a process for their preparation and to their use for the treatment and/or prevention of diseases which are associated with the modulation of SST receptors subtype 5.
- -
-
Page/Page column 23
(2009/01/20)
-
- Oxazole synthesis with minimal purification: Synthesis and application of a ROMPgel tosmic reagent
-
equations presented The synthesis of ring opening metathesis, polymer-supported Tosmic reagent 1 is described. This reagent was utilized in the conversion of aldehydes to oxazoles in good yields and purities.
- Barrett, Anthony G. M.,Cramp, Susan M.,Hennessy, Alan J.,Procopiou, Panayiotis A.,Roberts, Richard S.
-
p. 271 - 273
(2007/10/03)
-
- Benzotriazol-1-ylmethyl isocyanide, a new synthon for CH-N=C transfer. Syntheses of α-hydroxyaldehydes, 4-ethoxy-2-oxazolines and oxazoles
-
Readily prepared benzotriazol-1-ylmethyl isocyanide (BetMIC) reacts under mild conditions with ketones and aldehydes, to afford oxazolines (convertible into α-hydroxyaldehydes) and oxazoles, respectively.
- Katritzky,Chen,Yannakopoulou,Lue
-
p. 6657 - 6660
(2007/10/02)
-
