- Isoxazoles from 1,1-disubstituted bromoalkenes
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The regioselective synthesis of 3,5-disubstituted isoxazoles was achieved through the 1,3-dipolar cycloaddition of nitrile oxides with 1,1-disubstituted bromoalkenes. The substituted bromoalkenes function as alkyne synthons which were used to construct 5,
- Dadiboyena, Sureshbabu,Xu, Jianping,Hamme II, Ashton T.
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- Hypervalent iodine mediated synthesis of di- and tri-substituted isoxazoles via [3+2] cycloaddition of nitrile oxides
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An efficient and rapid protocol for the synthesis of 3,4-disubstituted and 3,4,5-trisubstituted isoxazoles under catalyst-free conditions is described. This protocol involves pre-oxidation of aldoxime into nitrile oxide using diacetoxyiodobenzene. The in
- Singhal, Ankur,Parumala, Santosh Kumar Reddy,Sharma, Arun,Peddinti, Rama Krishna
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- Methyl 3-Substituted-isoxazole-5- Carboxylates syntheses on solid supports via wang resin-bound 2,3-dibromopropionate
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A novel Wang resin-bound 2,3-dibromopropionate reagent has been developed and used as a potential dipolarophile for the facile preparation of methyl 3-substituted-isoxazole-5-carboxylates through triethylamine, promoting a sequence of reactions involving the in situ generation of 2-bromoacrylate resin and nitrile oxide, regioselective 1,3-dipolar cycloaddition, and loss of hydrogen bromide in one pot, and then cleavage from the resin with sodium methoxide. The advantages of this method include simple operation and mild conditions with good yield and high purity of the products. Copyright
- Sheng, Shou-Ri,He, Ai-Ying,Wei, Mei-Hong,Zhu, Ai-Li,Cai, Ming-Zhong
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- COMPOUNDS, COMPOSITIONS AND METHODS OF INCREASING CFTR ACTIVITY
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The present disclosure features compounds such as those having the Formulae (I) and (II), which can increase cystic fibrosis transmembrane conductance regulator (CFTR) activity as measured in human bronchial epithelial (hBE) cells. The present disclosure also features methods of treating a condition associated with decreased CFTR activity or a condition associated with a dysfunction of proteostasis comprising administering to a subject an effective amount of a disclosed compound, such as a compound of Formula (I) or (II).
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Paragraph 0245
(2017/02/24)
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- METHODS OF TREATING PULMONARY DISEASES AND DISORDERS
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The present disclosure features disclosed method of treating disorders such as COPD, bronchitis and/or asthma using disclosed compounds, optionally together with one or more additional active agents. Contemplated methods include administrating orally or by inhalation to a patient one or more disclosed compounds.
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Paragraph 0245
(2017/07/14)
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- COMPOUNDS, COMPOSITIONS, AND METHODS FOR INCREASING CFTR ACTIVITY
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The present disclosure is directed to disclosed compounds that increase cystic fibrosis transmembrane conductance regulator (CFTR) activity as measured in human bronchial epithelial (hBE) cells.
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Paragraph 0271
(2016/07/27)
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- ISOXAZOLE COMPOUNDS AND METHODS FOR THE TREATMENT OF CYSTIC FIBROSIS
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The invention relates to a compound of Formula (I) and methods of treating cystic fibrosis comprising the step of administering a therapeutically effective amount of a compound of Formula (I) or II to a patient in need thereof: Formula (I) and Formula (II). The invention relates to the use of substituted oxazole and substituted thiazole compounds in the treatment of cystic fibrosis transmembrane conductance regulator (CFTR) mediated diseases.
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Page/Page column 45; 46
(2016/04/26)
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- An environmentally benign synthesis of isoxazolines and isoxazoles mediated by potassium chloride in water
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An effective and environmentally benign procedure for the synthesis of isoxazolines and isoxazoles has been developed by a cycloaddition of nitrile oxides with alkenes or alkynes in water. In this approach, potassium chloride is first oxidized into chlorine in water by the environmentally friendly oxidant Oxone, then aldoximes are oxidized into nitrile oxides by the in situ generated hypochlorous acid, finally a 1,3-dipolar cycloaddition between nitrile oxides and alkenes or alkynes occurs to provide the corresponding isoxazolines and isoxazoles in good yields.
- Han, Liuquan,Zhang, Bijun,Zhu, Min,Yan, Jie
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supporting information
p. 2308 - 2311
(2014/04/17)
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- Solid-phase organic synthesis of methyl isoxazole-5-carboxylates based on wang resin-bound 1-phenylselenoacrylate
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A novel Wang resin-bound 1-phenylselenoacrylate reagent has been developed and used as dipolarophile for the 1,3-dipolar cycloaddition with nitrile oxides to the regioselective synthesis of methyl 3-substituted isoxazole-5-carboxylates in good yields and
- Tang, Ni,Sheng, Shou-Ri,Hu, Qiao-Sheng,Qu, Hong-En,Cai, Ming-Zhong
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experimental part
p. 3279 - 3287
(2012/09/08)
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- Generation of nitrile oxides from oximes using t -BuOI and their cycloaddition
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tert-Butyl hypoiodite (t-BuOI) was found to be a powerful reagent for the cycloaddition of oximes and alkenes/alkynes, leading to the formation of a variety of isoxazolines or isoxazoles under mild conditions.
- Minakata, Satoshi,Okumura, Sota,Nagamachi, Toshiki,Takeda, Youhei
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supporting information; experimental part
p. 2966 - 2969
(2011/07/07)
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- Novel non-peptidic vinylsulfones targeting the S2 and S3 subsites of parasite cysteine proteases
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We describe here the identification of non-peptidic vinylsulfones that inhibit parasite cysteine proteases in vitro and inhibit the growth of Trypanosoma brucei brucei parasites in culture. A high resolution (1.75 A) co-crystal structure of 8a bound to cruzain reveals how the non-peptidic P2/P3 moiety in such analogs bind the S2 and S3 subsites of the protease, effectively recapitulating important binding interactions present in more traditional peptide-based protease inhibitors and natural substrates.
- Bryant, Clifford,Kerr, Iain D.,Debnath, Moumita,Ang, Kenny K.H.,Ratnam, Joseline,Ferreira, Rafaela S.,Jaishankar, Priyadarshini,Zhao, DongMei,Arkin, Michelle R.,McKerrow, James H.,Brinen, Linda S.,Renslo, Adam R.
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scheme or table
p. 6218 - 6221
(2010/06/19)
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- Efficient access to isoxazoles from alkenes
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The direct regioselective synthesis of 3,5-disubstituted isoxazoles was achieved in one reaction vessel through a sequence of reactions involving the net bromination of an electron-deficient alkene, in situ generation of a nitrile oxide, 1,3-dipolar cycloaddition, and loss of HBr from an intermediate 5,5-disubstituted bromoisoxazoline. This one-pot process enables the synthesis of 3,5-disubstituted isoxazoles directly from electron-deficient alkenes thereby negating the isolation of the 1,1-disubstituted bromoalkene alkyne surrogate. Georg Thieme Verlag Stuttgart.
- Xu, Jianping,Hamme II, Ashton T.
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p. 919 - 923
(2008/12/22)
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- Conversion of oximes to carbonyl compounds by triscetylpyridinium tetrakis(oxodiperoxotungsto) phosphate (PCWP)-mediated oxidation with hydrogen peroxide
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Aromatic and aliphatic oximes have been deoximated in chloroform-water to the corresponding aldehydes with dilute hydrogen peroxide and triscetylpyridinium tetrakis (oxodiperoxotungsto) phosphate as catalyst. The presence of dipolarophiles in the reaction mixtures allows a competitive reaction that converts oximes into isoxazole and isoxazoline derivatives via the intermediate formation of nitrile oxide species.
- Ballistreri, Francesco P.,Chiacchio, Ugo,Rescifina, Antonio,Tomaselli, Gaetano,Toscano, Rosa M.
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p. 1230 - 1237
(2008/12/21)
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- Ramoplanin derivatives possessing antibacterial activity
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Novel ramoplanin derivatives are disclosed. These ramoplanin derivatives exhibit antibacterial activity. As the compounds of the subject invention exhibit potent activities against gram positive bacteria, they are useful antimicrobial agents. Methods of synthesis and of use of the compounds are also disclosed.
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Page/Page column 39; 48
(2010/11/23)
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- DFT-HSAB prediction of regioselectivity in 1,3-dipolar cycloadditions: Behavior of (4-substituted)benzonitrile oxides towards methyl propiolate
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The regioselectivity of 1.3-di-polar cycloadditions between (4-substituted)benzonitrile oxides and methyl propiolate cannot be rationalized on the basis of the electron demand of the reactants or frontier molecular-orbital theory. To this problem, we have
- Ponti, Alessandro,Molteni, Giorgio
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p. 1156 - 1161
(2007/10/03)
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- Regioisomeric 5(3)-aminomethyl-3(5)-phenylisoxazoles: Synthesis, spectroscopic discrimination, and muscarinic activity
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The regioselective synthesis of isomeric 5(3)-aminomethyl-3(5)-phenyl isoxazoles using different methods is described. Spectroscopic data, especially mass spectrometric fragmentation, were used to identify and characterize the regioisomers. The muscarinic
- Dannhardt,Lambrecht,Laufer,Mutschler,Schweiger
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p. 437 - 443
(2007/10/02)
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- SYNTHESIS AND PROPERTIES OF AZOLS AND THEIR DERIVATIVES. PART V. REGIOCHEMISTRY IN CYCLOADDITION REACTIONS OF BENZONITRILE N-OXIDE WITH β-SUBSTITUTED NITROETHYLENES
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The cycloaddition reactions of benzonitrile N-oxide with β-substituted nitroethylenes have been investigated.It was found that the regiochemistry of these reactions depended on the nature of β-substituents.
- Baranski, Andrzej
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p. 257 - 266
(2007/10/02)
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- Regioselectivity in cycloaddition reactions on solid phases
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A 1percent crosslinked divinylbenzene-styrene copolymer, incorporating benzyl acrylate groups, reacted in normal Diels-Alder reactions with E-1-phenyl-1,3-butadiene or methyl E-2,4-pentadienoate to give their respective polymer-bound benzyl cyclohexenecarboxylates.Polymer-bound benzyl propiolate and polymer-bound benzyl phenylpropiolate reacted with benzonitrile oxide in a typical 1,3-dipolar addition reaction to give their respective polymer-bound isoxazoles.Cleavage of the polymer-bound Diels-Alder adducts and the polymer-bound 1,3-dipolar addition adduct derived from polymer-bound benzyl propiolate gave mixtures of ortho and meta regiomers similar to those produced in analogous reactions in solution.Cleavage of the polymer-bound 1,3-dipolar addition adduct, derived from polymer-bound benzyl phenylpropiolate, followed by esterification, gave a solitary adduct, 4-carbomethoxy-3,5-diphenylisoxazole, but an analogous solution 1,3-dipolar addition yielded a 1:1 ratio of the two possible regiomers.
- Yedidia, Varda,Leznoff, Clifford C.
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p. 1144 - 1150
(2007/10/02)
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