Heterocyclic Building Blocks-Isothiazole

Catalytic enantioselective synthesis of 3-substituted benzosultams via Corey-Bakshi-Shibata reduction of cyclic N-sulfonylimines was written by Enders, Dieter;Seppelt, Matthias. And the article was included in Synlett in 2011.Product Details of 62473-92-1 This article mentions the following:

The catalytic asym. synthesis of 3-substituted benzo-fused sultams I (R¹ = Me, Et, n-Bu, Ph; R² = H, Br) in good to excellent yields of 74-95% and enantiomeric excesses of 69-94% by the Corey-Bakshi-Shibata reduction of the corresponding cyclic N-sulfonylimines with catecholborane is reported. In the experiment, the researchers used many compounds, for example, 6-Bromobenzo[d]isothiazol-3(2H)-one 1,1-dioxide (cas: 62473-92-1Product Details of 62473-92-1).

6-Bromobenzo[d]isothiazol-3(2H)-one 1,1-dioxide (cas: 62473-92-1) belongs to isothiazole derivatives. Isothiazoles and their saturated and/or oxygenated analogs play an important role in pharmaceutical research. 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.Product Details of 62473-92-1

Referemce:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

Metformin for early comorbid glucose dysregulation and schizophrenia spectrum disorders: a pilot double-blind randomized clinical trial was written by Agarwal, Sri Mahavir;Panda, Roshni;Costa-Dookhan, Kenya A.;MacKenzie, Nicole E.;Treen, Quinn Casuccio;Caravaggio, Fernando;Hashim, Eyesha;Leung, General;Kirpalani, Anish;Matheson, Kelly;Chintoh, Araba F.;Kramer, Caroline K.;Voineskos, Aristotle N.;Graff-Guerrero, Ariel;Remington, Gary J.;Hahn, Margaret K.. And the article was included in Translational Psychiatry in 2021.Reference of 146939-27-7 This article mentions the following:

Patients with schizophrenia have exceedingly high rates of metabolic comorbidity including type 2 diabetes and lose 15-20 years of life due to cardiovascular diseases, with early accrual of cardiometabolic disease. In this study, thirty overweight or obese (Body Mass Index (BMI) > 25) participants under 40 years old with schizophrenia spectrum disorders and early comorbid prediabetes or type 2 diabetes receiving antipsychotic medications were randomized, in a double-blind fashion, to metformin 1500 mg/day or placebo (2:1 ratio; n = 21 metformin and n = 9 placebo) for 4 mo. The primary outcome measures were improvements in glucose homeostasis (HbA1c, fasting glucose) and insulin resistance (Matsuda index-derived from oral glucose tolerance tests and homeostatic model of insulin resistance (HOMA-IR)). Secondary outcome measures included changes in weight, MRI measures of fat mass and distribution, symptom severity, cognition, and hippocampal volume Twenty-two patients (n = 14 metformin; n = 8 placebo) completed the trial. The metformin group had a significant decrease over time in the HOMA-IR (p = 0.043) and fasting blood glucose (p = 0.007) vs. placebo. There were no differences between treatment groups in the Matsuda index, HbA1c, which could suggest liver-specific effects of metformin. There were no between group differences in other secondary outcome measures, while weight loss in the metformin arm correlated significantly with decreases in s.c., but not visceral or hepatic adipose tissue. Our results show that metformin improved dysglycemia and insulin sensitivity, independent of weight loss, in a young population with prediabetes/diabetes and psychosis spectrum illness, that is at extremely high risk of early cardiovascular mortality. In the experiment, the researchers used many compounds, for example, 5-(2-(4-(Benzo[d]isothiazol-3-yl)piperazin-1-yl)ethyl)-6-chloroindolin-2-one (cas: 146939-27-7Reference of 146939-27-7).

5-(2-(4-(Benzo[d]isothiazol-3-yl)piperazin-1-yl)ethyl)-6-chloroindolin-2-one (cas: 146939-27-7) belongs to isothiazole derivatives. The chemistry of isothiazoles is being intensively developed, which is evidenced by the wide range of selective transformations involving the isothiazole heterocycle and the high biological activity of its derivatives that can be used as effective new drugs and plant protection chemicals. Many compounds with an isothiazole scaffold demonstrated a wide range of biological profiles, including antiinflammatory, antithrombotic, and anticonvulsive agents.Reference of 146939-27-7

Referemce:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

The Total Synthesis of (-)-Lemonomycin was written by Ashley, Eric R.;Cruz, Ernest G.;Stoltz, Brian M.. And the article was included in Journal of the American Chemical Society in 2003.Synthetic Route of C13H19NO3S This article mentions the following:

The first total synthesis of the novel glycosylated tetrahydroisoquinoline antitumor antibiotic (-)-Lemonomycin I has been accomplished. The highly convergent synthesis relies on a key asym. dipolar cycloaddition to set the stereochem. of the aglycon core, a Suzuki fragment coupling to connect the diazabicycle to the aryl subunit, and a stereoselective Pictet-Spengler reaction that incorporates the aminoglycoside subunit directly into the core structure without the need for late-stage glycosylation or protecting group manipulations. The novel aminoglycoside was prepared using a highly diastereoselective Felkin-controlled acetate aldol addition reaction to a threonine-derived ketone. 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)prop-2-en-1-one (cas: 119944-89-7Synthetic Route of C13H19NO3S).

1-((3aR,6S,7aS)-8,8-Dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)prop-2-en-1-one (cas: 119944-89-7) 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. It has been found that isothiazole-based compounds show synergistic effects when used with other biocidal compounds.Synthetic Route of C13H19NO3S

Referemce:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

Second-generation antipsychotics and pregnancy complications was written by Ellfolk, Maria;Leinonen, Maarit K.;Gissler, Mika;Lahesmaa-Korpinen, Anna-Maria;Saastamoinen, Leena;Nurminen, Marja-Leena;Malm, Heli. And the article was included in European Journal of Clinical Pharmacology in 2020.Safety of 5-(2-(4-(Benzo[d]isothiazol-3-yl)piperazin-1-yl)ethyl)-6-chloroindolin-2-one This article mentions the following:

To study if second-generation antipsychotic (S-GA) use during pregnancy is associated with an increased risk of pregnancy and neonatal complications. A population-based birth cohort study using national register data extracted from the “Drugs and Pregnancy” database in Finland, years 1996-2016. The sampling frame included 1,181,090 pregnant women and their singleton births. Women were categorized into three groups: exposed to S-GAs during pregnancy (n = 4225), exposed to first-generation antipsychotics (F-GAs) during pregnancy (n = 1576), and unexposed (no purchases of S-GAs or F-GAs during pregnancy, n = 21,125). Pregnancy outcomes in S-GA users were compared with those in the two comparison groups using multiple logistic regression models. Comparing S-GA users with unexposed ones, the risk was increased for gestational diabetes (adjusted odds ratio, OR 1.43; 95% CI 1.25-1.65), cesarean section (OR 1.35; 95% CI 1.18-1.53), being born large for gestational age (LGA) (OR 1.57; 95% CI 1.14-2.16), and preterm birth (OR 1.29; 95% CI 1.03-1.62). The risk for these outcomes increased further with continuous S-GA use. Infants in the S-GA group were also more likely to suffer from neonatal complications. Comparing S-GA users with the F-GA group, the risk of cesarean section and LGA was higher (OR 1.25, 95% CI 1.03-1.51; and OR 1.89, 95% CI 1.20-2.99, resp.). Neonatal complications did not differ between the S-GA and F-GA groups. Prenatal exposure to S-GAs is associated with an increased risk of pregnancy complications related to impaired glucose metabolism Neonatal problems are common and occur similarly in S-GA and F-GA users. In the experiment, the researchers used many compounds, for example, 5-(2-(4-(Benzo[d]isothiazol-3-yl)piperazin-1-yl)ethyl)-6-chloroindolin-2-one (cas: 146939-27-7Safety of 5-(2-(4-(Benzo[d]isothiazol-3-yl)piperazin-1-yl)ethyl)-6-chloroindolin-2-one).

5-(2-(4-(Benzo[d]isothiazol-3-yl)piperazin-1-yl)ethyl)-6-chloroindolin-2-one (cas: 146939-27-7) belongs to isothiazole derivatives. The chemistry of isothiazoles is being intensively developed, which is evidenced by the wide range of selective transformations involving the isothiazole heterocycle and the high biological activity of its derivatives that can be used as effective new drugs and plant protection chemicals. 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.Safety of 5-(2-(4-(Benzo[d]isothiazol-3-yl)piperazin-1-yl)ethyl)-6-chloroindolin-2-one

Referemce:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

Asymmetric synthesis of chiral piperazinylpropylisoxazoline ligands for dopamine receptors was written by Jung, Ji Young;Jung, Sun Ho;Koh, Hun Yeong. And the article was included in European Journal of Medicinal Chemistry in 2007.SDS of cas: 119944-89-7 This article mentions the following:

The asym. synthesis of chiral piperazinylpropylisoxazoline analogs, e.g., I and II, was accomplished through a seven-step sequence of reactions, which involved asym. 1,3-dipolar cycloaddition, alkyl chain extension, and reductive amination as key reactions. Chiral ligands I and II exhibited the higher binding affinity and selectivity for the D₃ receptor over the D₄ receptor than their enantiomers, resp. 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)prop-2-en-1-one (cas: 119944-89-7SDS of cas: 119944-89-7).

1-((3aR,6S,7aS)-8,8-Dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)prop-2-en-1-one (cas: 119944-89-7) 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. The ring structure of isothiazole is incorporated into larger compounds with biological activity such as the pharmaceutical drugs ziprasidone and perospirone.SDS of cas: 119944-89-7

Referemce:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

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

On the scope of diastereoselective epoxidation of various chiral auxiliaries derived enones: The conformational analysis of camphor derived N- and O-enones was written by Lee, Wei-Der;Chiu, Ching-Chen;Hsu, Hua-Lin;Chen, Kwunmin. And the article was included in Tetrahedron in 2004.Electric Literature of C13H19NO3S This article mentions the following:

Various camphor derived N- and O-enones were treated with selected oxidants to provide the corresponding epoxides in a wide range of diastereoselectivity. For camphorsultam derived activated alkenes, high to excellent stereoselectivities were obtained when the s-trans enones were treated with methyl(trifluoromethyl)dioxirane. On the other hand, for exo-10,10-diphenyl-2,10-camphanediol and exo-10,10-diphenyl-10-methoxy-2-camphanol derived alkenes, the use of s-cis enones gave the desired epoxide with excellent diastereoselectivity under the same reaction conditions. The stereoselectivity was highly dependent on the geometry of the auxiliaries derived enones and the stereochem. induction is discussed. In the experiment, the researchers used many compounds, for example, 1-((3aS,6R,7aR)-8,8-Dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)prop-2-en-1-one (cas: 94594-91-9Electric Literature of C13H19NO3S).

1-((3aS,6R,7aR)-8,8-Dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)prop-2-en-1-one (cas: 94594-91-9) belongs to isothiazole derivatives. The chemistry of isothiazoles is being intensively developed, which is evidenced by the wide range of selective transformations involving the isothiazole heterocycle and the high biological activity of its derivatives that can be used as effective new drugs and plant protection chemicals. Various penicillins and cephalosporins having an isothiazole ring system have shown considerable antibacterial efficacy against Gram-positive and Gram-negative bacteria.Electric Literature of C13H19NO3S

Referemce:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

Determination of 3 isothiazolinone preservatives in water-based adhesive by LC-MS/MS method was written by Lu, Xinbo;Xiao, Weiqiang;Xu, Gaoyan;Shi, Chunyun;Jiang, Jian;Zhou, Guojun. And the article was included in Zhongguo Yancao Xuebao in 2015.Product Details of 1003-07-2 This article mentions the following:

A method for determining 3 isothiazolinone preservatives in water-based adhesive by high performance liquid chromatog. tandem mass spectrometry (LC-MS/MS) was developed. The sample was extracted with water, centrifuged, and then analyzed by LCMS/MS and quantified by internal standard method. Results showed that: the linear relationship was good with determination coefficients R² ≥ 0.9996 in the MI and CMI concentration range of 2.5∼250 ng/mL and in the BIT concentration range of 5∼500 ng/mL. The recoveries of standard addition ranged from 96.3% to 109.6% with relative standard deviation (RSD) of 1.5%∼6.7%. The limit of detection was between 0.011 and 0.015 mg/kg, and that of quantification was between 0.035 and 0.051 mg/kg. It was concluded that this method was suitable for the determination of 3 isothiazolinone preservatives in water-based adhesive. In the experiment, the researchers used many compounds, for example, Isothiazol-3(2H)-one (cas: 1003-07-2Product Details of 1003-07-2).

Isothiazol-3(2H)-one (cas: 1003-07-2) belongs to isothiazole derivatives. Isothiazoles and their saturated and/or oxygenated analogs play an important role in pharmaceutical research. 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.Product Details of 1003-07-2

Referemce:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com

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

Causes of malfunctions of RO sewage treatment plant and countermeasures was written by Xiong, Qiwu;Chang, Kai. And the article was included in Zhongwai Nengyuan in 2013.SDS of cas: 1003-07-2 This article mentions the following:

Sinopec Yanshan Company’s 1200 m³/h ultra-filtration reverse osmosis sewage treatment plant met with a serious fault after nearly six years of stable operation. The RO membrane was seriously contaminated, resulting in a steep decline in output of treated water. Anal. showed that RO membrane blockage was the main cause of this breakdown, which resulted from the rapid growth of microorganism at high temperatures in summer days and the precipitation of salt due to high contents of inorganic salts in the water being treated, such as iron, manganese and aluminum. Based on field experiment results and actual production conditions, technicians proposed and took countermeasures, including adding inoxidable bactericides (isothiazolinone and DBNPA; dosing method: impact mode + continuous low-concentration dosing; dose: about 100 mg/L), adding new type of scale inhibitor (dose: about 3 mg/L), increasing the use of sodium hypochlorite (residual chlorine in concentrated water controlled between 0.5 and 0.8 mg/L), controlling the use of polyaluminum chloride between 10 and 14 mg/L, and optimizing chem. cleaning schemes. After the above measures were taken, the contaminants on the RO membrane were brought under control and the performance of the membrane recovered. More than 70% of manganese ions were removed. The operation cycle of the sewage treatment plant was extended to about 20 days from seven days and output of treated water increased by 5 × 10⁴t per mo. In the experiment, the researchers used many compounds, for example, Isothiazol-3(2H)-one (cas: 1003-07-2SDS of cas: 1003-07-2).

Isothiazol-3(2H)-one (cas: 1003-07-2) 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.SDS of cas: 1003-07-2

Referemce:
Isothiazole – Wikipedia,
Isothiazole – ScienceDirect.com