Tag: 271.3757

Steadman, Victoria A. et al. published their research in Journal of Medicinal Chemistry in 2017 | CAS: 128947-19-3

1-((3aR,6S,7aS)-8,8-Dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)propan-1-one (cas: 128947-19-3) belongs to isothiazole derivatives. Similar to other five-membered heterocycles, isothiazoles react with a wide range of electrophilic and nucleophilic reagents to form diverse products. Various penicillins and cephalosporins having an isothiazole ring system have shown considerable antibacterial efficacy against Gram-positive and Gram-negative bacteria.Electric Literature of C13H21NO3S

Discovery of Potent Cyclophilin Inhibitors Based on the Structural Simplification of Sanglifehrin A was written by Steadman, Victoria A.;Pettit, Simon B.;Poullennec, Karine G.;Lazarides, Linos;Keats, Andrew J.;Dean, David K.;Stanway, Steven J.;Austin, Carol A.;Sanvoisin, Jonathan A.;Watt, Gregory M.;Fliri, Hans G.;Liclican, Albert C.;Jin, Debi;Wong, Melanie H.;Leavitt, Stephanie A.;Lee, Yu-Jen;Tian, Yang;Frey, Christian R.;Appleby, Todd C.;Schmitz, Uli;Jansa, Petr;Mackman, Richard L.;Schultz, Brian E.. And the article was included in Journal of Medicinal Chemistry in 2017.Electric Literature of C13H21NO3S This article mentions the following:

Cyclophilin inhibition has been a target for the treatment of hepatitis C and other diseases, but the generation of potent, drug-like mols. through chem. synthesis has been challenging. In this study, a set of macrocyclic cyclophilin inhibitors was synthesized based on the core structure of the natural product sanglifehrin A. Initial compound optimization identified the valine-m-tyrosine-piperazic acid tripeptide (Val-m-Tyr-Pip) in the sanglifehrin core, stereocenters at C14 and C15, and the hydroxyl group of the m-tyrosine (m-Tyr) residue as key contributors to compound potency. Replacing the C18-C21 diene unit of sanglifehrin with a styryl group led to potent compounds that displayed a novel binding mode in which the styrene moiety engaged in a π-stacking interaction with Arg55 of cyclophilin A (Cyp A), and the m-Tyr residue was displaced into solvent. This observation allowed further simplifications of the scaffold to generate new lead compounds in the search for orally bioavailable cyclophilin inhibitors. In the experiment, the researchers used many compounds, for example, 1-((3aR,6S,7aS)-8,8-Dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)propan-1-one (cas: 128947-19-3Electric Literature of C13H21NO3S).

1-((3aR,6S,7aS)-8,8-Dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)propan-1-one (cas: 128947-19-3) belongs to isothiazole derivatives. Similar to other five-membered heterocycles, isothiazoles react with a wide range of electrophilic and nucleophilic reagents to form diverse products. Various penicillins and cephalosporins having an isothiazole ring system have shown considerable antibacterial efficacy against Gram-positive and Gram-negative bacteria.Electric Literature of C13H21NO3S

Referemce:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

Han, Fangzhi et al. published their research in Organic Letters in 2021 | CAS: 128947-19-3

1-((3aR,6S,7aS)-8,8-Dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)propan-1-one (cas: 128947-19-3) belongs to isothiazole derivatives. Isothiazoles and benzisothiazoles are usually liquids or low-melting-point solids; polar substituents increase the melting points because of the possibility of hydrogen bonding and other interactions in the crystalline state. Many compounds with an isothiazole scaffold demonstrated a wide range of biological profiles. Some of these molecules have been efficiently used in the treatment of Alzheimer’s disease.Electric Literature of C13H21NO3S

Total synthesis and determination of the absolute configuration of Rakicidin C was written by Han, Fangzhi;Liu, Guangju;Jin, Chaofan;Wang, Jinghan;Liu, Jianwei;Wang, Liang;Chen, Yue. And the article was included in Organic Letters in 2021.Electric Literature of C13H21NO3S This article mentions the following:

The absolute configuration of rakicidin C was predicted by comparison of optical rotation data and absolute configuration of APD-cyclic depsipeptides and further determined by total synthesis. The absolute configuration of five chiral centers was determined as 2R, 15R, 16R, 17S, and 19S. Our efficient route involves 19 longest linear steps with an overall yield of 1.49%. In the experiment, the researchers used many compounds, for example, 1-((3aR,6S,7aS)-8,8-Dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)propan-1-one (cas: 128947-19-3Electric Literature of C13H21NO3S).

1-((3aR,6S,7aS)-8,8-Dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)propan-1-one (cas: 128947-19-3) belongs to isothiazole derivatives. Isothiazoles and benzisothiazoles are usually liquids or low-melting-point solids; polar substituents increase the melting points because of the possibility of hydrogen bonding and other interactions in the crystalline state. Many compounds with an isothiazole scaffold demonstrated a wide range of biological profiles. Some of these molecules have been efficiently used in the treatment of Alzheimer’s disease.Electric Literature of C13H21NO3S

Referemce:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

Moumne, Roba et al. published their research in European Journal of Organic Chemistry in 2007 | CAS: 128947-19-3

1-((3aR,6S,7aS)-8,8-Dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)propan-1-one (cas: 128947-19-3) belongs to isothiazole derivatives. Similar to other five-membered heterocycles, isothiazoles react with a wide range of electrophilic and nucleophilic reagents to form diverse products. Isothiazoles are readily prepared from isoxazoles. Thus, reductive ring opening of isoxazoles gives enaminones , which on treatment with phosphorus pentasulfide and chloranil give the corresponding isothiazoles.Quality Control of 1-((3aR,6S,7aS)-8,8-Dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)propan-1-one

New scalable asymmetric aminomethylation reaction for the synthesis of β2-amino acids was written by Moumne, Roba;Denise, Bernard;Guitot, Karine;Rudler, Henri;Lavielle, Solange;Karoyan, Philipe. And the article was included in European Journal of Organic Chemistry in 2007.Quality Control of 1-((3aR,6S,7aS)-8,8-Dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)propan-1-one This article mentions the following:

β-Amino acids are useful tools in the design of peptidomimetics, and the development of new methods for their syntheses, particularly the synthesis of β2-amino acids, remains an important challenge. Here a scalable route based on the aminomethylation of silyl ketene N,O-acetals by Mannich-type iminium electrophiles was reported. Using this method, a series of N-Boc protected β-amino acids were obtained in good yields and high enantioselectivities. In the experiment, the researchers used many compounds, for example, 1-((3aR,6S,7aS)-8,8-Dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)propan-1-one (cas: 128947-19-3Quality Control of 1-((3aR,6S,7aS)-8,8-Dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)propan-1-one).

1-((3aR,6S,7aS)-8,8-Dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)propan-1-one (cas: 128947-19-3) belongs to isothiazole derivatives. Similar to other five-membered heterocycles, isothiazoles react with a wide range of electrophilic and nucleophilic reagents to form diverse products. Isothiazoles are readily prepared from isoxazoles. Thus, reductive ring opening of isoxazoles gives enaminones , which on treatment with phosphorus pentasulfide and chloranil give the corresponding isothiazoles.Quality Control of 1-((3aR,6S,7aS)-8,8-Dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)propan-1-one

Referemce:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

Garcia-Fortanet, Jorge et al. published their research in Chemistry – A European Journal in 2007 | CAS: 128947-19-3

1-((3aR,6S,7aS)-8,8-Dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)propan-1-one (cas: 128947-19-3) belongs to isothiazole derivatives. Isothiazole is a good solvent for many organic substances but should be used with caution because it is more toxic than pyridine. It has been found that isothiazole-based compounds show synergistic effects when used with other biocidal compounds.Product Details of 128947-19-3

The total synthesis and biological properties of the cytotoxic macrolide FD-891 and its non-natural (Z)-C12 isomer was written by Garcia-Fortanet, Jorge;Murga, Juan;Carda, Miguel;Marco, J. Alberto;Matesanz, Ruth;Diaz, J. Fernando;Barasoain, Isabel. And the article was included in Chemistry – A European Journal in 2007.Product Details of 128947-19-3 This article mentions the following:

A total, stereoselective synthesis of the naturally occurring, cytotoxic macrolide FD-891 (I) and of its non-natural (Z)-C12 isomer is described. Three fragments of the main carbon chain were stereoselectively prepared by using asym. aldol and allylation reactions as the key steps. The mol. was then assembled by using two Julia-Kocienski olefinations to connect the three fragments and a Yamaguchi reaction to close the macrolactone ring. Some specific biol. properties (cytotoxicity, binding to tubulin) have been determined for both macrolides. The E configuration of the C12-C13 olefinic bond seems to be an important feature in determining the cytotoxicity but the precise biol. mechanism of the latter still remains to be cleared. In the experiment, the researchers used many compounds, for example, 1-((3aR,6S,7aS)-8,8-Dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)propan-1-one (cas: 128947-19-3Product Details of 128947-19-3).

1-((3aR,6S,7aS)-8,8-Dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)propan-1-one (cas: 128947-19-3) belongs to isothiazole derivatives. Isothiazole is a good solvent for many organic substances but should be used with caution because it is more toxic than pyridine. It has been found that isothiazole-based compounds show synergistic effects when used with other biocidal compounds.Product Details of 128947-19-3

Referemce:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

Berkhan, Gesche et al. published their research in Angewandte Chemie, International Edition in 2016 | CAS: 128947-19-3

1-((3aR,6S,7aS)-8,8-Dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)propan-1-one (cas: 128947-19-3) belongs to isothiazole derivatives. Isothiazoles and benzisothiazoles are usually liquids or low-melting-point solids; polar substituents increase the melting points because of the possibility of hydrogen bonding and other interactions in the crystalline state. In general, isothiazole undergoes nitration in the presence of HNO3, sulfuric acid, and sulfonation by using sulfuric acid under thermal conditions to generate corresponding 4-nitro- and 4-sulfonic acid derivatives, respectively.Quality Control of 1-((3aR,6S,7aS)-8,8-Dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)propan-1-one

The interplay between a multifunctional dehydratase domain and a C-methyltransferase effects olefin shift in ambruticin biosynthesis was written by Berkhan, Gesche;Merten, Christian;Holec, Claudia;Hahn, Frank. And the article was included in Angewandte Chemie, International Edition in 2016.Quality Control of 1-((3aR,6S,7aS)-8,8-Dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)propan-1-one This article mentions the following:

The olefin shift is an important modification during polyketide biosynthesis. Particularly for type I cis-AT PKS, little information has been gained on the enzymic mechanisms involved. We present our in vitro investigations on the olefin shift occurring during ambruticin biosynthesis. The unique, multifunctional domain AmbDH4 catalyzes consecutive dehydration, epimerization, and enoyl isomerization. The resulting 3-enethioate is removed from the equilibrium by α-methylation catalyzed by the highly specific C-methyltransferase AmbM. This thermodynamically unfavorable overall process is enabled by the high, concerted substrate specificity of the involved enzymes. AmbDH4 shows close relationship to DH domains and initial mechanistic studies suggest that the olefin shift occurs via a similar proton-shuttling mechanism as previously described for EI domains from trans-AT-PKS. In the experiment, the researchers used many compounds, for example, 1-((3aR,6S,7aS)-8,8-Dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)propan-1-one (cas: 128947-19-3Quality Control of 1-((3aR,6S,7aS)-8,8-Dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)propan-1-one).

1-((3aR,6S,7aS)-8,8-Dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)propan-1-one (cas: 128947-19-3) belongs to isothiazole derivatives. Isothiazoles and benzisothiazoles are usually liquids or low-melting-point solids; polar substituents increase the melting points because of the possibility of hydrogen bonding and other interactions in the crystalline state. In general, isothiazole undergoes nitration in the presence of HNO3, sulfuric acid, and sulfonation by using sulfuric acid under thermal conditions to generate corresponding 4-nitro- and 4-sulfonic acid derivatives, respectively.Quality Control of 1-((3aR,6S,7aS)-8,8-Dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)propan-1-one

Referemce:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

Garcia-Fortanet, Jorge et al. published their research in Organic Letters in 2006 | CAS: 128947-19-3

1-((3aR,6S,7aS)-8,8-Dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)propan-1-one (cas: 128947-19-3) belongs to isothiazole derivatives. Similar to other five-membered heterocycles, isothiazoles react with a wide range of electrophilic and nucleophilic reagents to form diverse products. Many compounds with an isothiazole scaffold demonstrated a wide range of biological profiles. Some of these molecules have been efficiently used in the treatment of Alzheimer’s disease.Application In Synthesis of 1-((3aR,6S,7aS)-8,8-Dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)propan-1-one

Stereoselective Synthesis of the Cytotoxic Macrolide FD-891 was written by Garcia-Fortanet, Jorge;Murga, Juan;Carda, Miguel;Marco, J. Alberto. And the article was included in Organic Letters in 2006.Application In Synthesis of 1-((3aR,6S,7aS)-8,8-Dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)propan-1-one This article mentions the following:

A total synthesis of the naturally occurring, cytotoxic macrolide FD-891 (I) is described. Three fragments were first stereoselectively constructed using mainly asym. aldol and allylation reactions. The complete framework was then assembled using two Julia-Kocienski olefinations to connect the three fragments and a Yamaguchi reaction to close the macrolactone ring. In the experiment, the researchers used many compounds, for example, 1-((3aR,6S,7aS)-8,8-Dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)propan-1-one (cas: 128947-19-3Application In Synthesis of 1-((3aR,6S,7aS)-8,8-Dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)propan-1-one).

1-((3aR,6S,7aS)-8,8-Dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)propan-1-one (cas: 128947-19-3) belongs to isothiazole derivatives. Similar to other five-membered heterocycles, isothiazoles react with a wide range of electrophilic and nucleophilic reagents to form diverse products. Many compounds with an isothiazole scaffold demonstrated a wide range of biological profiles. Some of these molecules have been efficiently used in the treatment of Alzheimer’s disease.Application In Synthesis of 1-((3aR,6S,7aS)-8,8-Dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)propan-1-one

Referemce:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

Garcia-Fortanet, Jorge et al. published their research in Chemistry – A European Journal in 2007 | CAS: 128947-19-3

1-((3aR,6S,7aS)-8,8-Dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)propan-1-one (cas: 128947-19-3) belongs to isothiazole derivatives. Isothiazole is a good solvent for many organic substances but should be used with caution because it is more toxic than pyridine. It has been found that isothiazole-based compounds show synergistic effects when used with other biocidal compounds.Product Details of 128947-19-3

The total synthesis and biological properties of the cytotoxic macrolide FD-891 and its non-natural (Z)-C12 isomer was written by Garcia-Fortanet, Jorge;Murga, Juan;Carda, Miguel;Marco, J. Alberto;Matesanz, Ruth;Diaz, J. Fernando;Barasoain, Isabel. And the article was included in Chemistry – A European Journal in 2007.Product Details of 128947-19-3 This article mentions the following:

A total, stereoselective synthesis of the naturally occurring, cytotoxic macrolide FD-891 (I) and of its non-natural (Z)-C12 isomer is described. Three fragments of the main carbon chain were stereoselectively prepared by using asym. aldol and allylation reactions as the key steps. The mol. was then assembled by using two Julia-Kocienski olefinations to connect the three fragments and a Yamaguchi reaction to close the macrolactone ring. Some specific biol. properties (cytotoxicity, binding to tubulin) have been determined for both macrolides. The E configuration of the C12-C13 olefinic bond seems to be an important feature in determining the cytotoxicity but the precise biol. mechanism of the latter still remains to be cleared. In the experiment, the researchers used many compounds, for example, 1-((3aR,6S,7aS)-8,8-Dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)propan-1-one (cas: 128947-19-3Product Details of 128947-19-3).

1-((3aR,6S,7aS)-8,8-Dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)propan-1-one (cas: 128947-19-3) belongs to isothiazole derivatives. Isothiazole is a good solvent for many organic substances but should be used with caution because it is more toxic than pyridine. It has been found that isothiazole-based compounds show synergistic effects when used with other biocidal compounds.Product Details of 128947-19-3

Referemce:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

Berkhan, Gesche et al. published their research in Angewandte Chemie, International Edition in 2016 | CAS: 128947-19-3

1-((3aR,6S,7aS)-8,8-Dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)propan-1-one (cas: 128947-19-3) belongs to isothiazole derivatives. Isothiazoles and benzisothiazoles are usually liquids or low-melting-point solids; polar substituents increase the melting points because of the possibility of hydrogen bonding and other interactions in the crystalline state. In general, isothiazole undergoes nitration in the presence of HNO3, sulfuric acid, and sulfonation by using sulfuric acid under thermal conditions to generate corresponding 4-nitro- and 4-sulfonic acid derivatives, respectively.Quality Control of 1-((3aR,6S,7aS)-8,8-Dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)propan-1-one

The interplay between a multifunctional dehydratase domain and a C-methyltransferase effects olefin shift in ambruticin biosynthesis was written by Berkhan, Gesche;Merten, Christian;Holec, Claudia;Hahn, Frank. And the article was included in Angewandte Chemie, International Edition in 2016.Quality Control of 1-((3aR,6S,7aS)-8,8-Dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)propan-1-one This article mentions the following:

The olefin shift is an important modification during polyketide biosynthesis. Particularly for type I cis-AT PKS, little information has been gained on the enzymic mechanisms involved. We present our in vitro investigations on the olefin shift occurring during ambruticin biosynthesis. The unique, multifunctional domain AmbDH4 catalyzes consecutive dehydration, epimerization, and enoyl isomerization. The resulting 3-enethioate is removed from the equilibrium by α-methylation catalyzed by the highly specific C-methyltransferase AmbM. This thermodynamically unfavorable overall process is enabled by the high, concerted substrate specificity of the involved enzymes. AmbDH4 shows close relationship to DH domains and initial mechanistic studies suggest that the olefin shift occurs via a similar proton-shuttling mechanism as previously described for EI domains from trans-AT-PKS. In the experiment, the researchers used many compounds, for example, 1-((3aR,6S,7aS)-8,8-Dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)propan-1-one (cas: 128947-19-3Quality Control of 1-((3aR,6S,7aS)-8,8-Dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)propan-1-one).

1-((3aR,6S,7aS)-8,8-Dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)propan-1-one (cas: 128947-19-3) belongs to isothiazole derivatives. Isothiazoles and benzisothiazoles are usually liquids or low-melting-point solids; polar substituents increase the melting points because of the possibility of hydrogen bonding and other interactions in the crystalline state. In general, isothiazole undergoes nitration in the presence of HNO3, sulfuric acid, and sulfonation by using sulfuric acid under thermal conditions to generate corresponding 4-nitro- and 4-sulfonic acid derivatives, respectively.Quality Control of 1-((3aR,6S,7aS)-8,8-Dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)propan-1-one

Referemce:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com