Heterocyclic Building Blocks-Thiazolidine

Molecular diversity of the three-component reaction of α-amino acids, dialkyl acetylenedicarboxylates and N-substituted maleimides was written by Chen, Liang;Sun, Jing;Xie, Ju;Yan, Chao-Guo. And the article was included in Organic & Biomolecular Chemistry in 2016.Computed Properties of C4H7NO2S This article mentions the following:

The one-pot three-component reaction of secondary α-amino acids, including proline, thiazolidine-4-carboxylic acid, piperidine-2-carboxylic acid and sarcosine with dialkyl acetylenedicarboxylate and N-substituted maleimides in refluxing ethanol afforded functionalized pyrrolo[3,4-a]pyrrolizines, pyrrolo[3′,4′:3,4]pyrrolo[1,2-c]thiazoles, pyrrolo[3,4-a]indolizines and octahydropyrrolo[3,4-c]pyrroles in good yields and with high diastereoselectivity. On the other hand, the similar three-component reaction containing primary α-amino acids, such as glycine, alanine, phenylalanine and leucine, with N-substituted maleimides and two mols. of dialkyl acetylenedicarboxylate gave the corresponding (hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)maleates. In the experiment, the researchers used many compounds, for example, Thiazolidine-4-carboxylic acid (cas: 444-27-9Computed Properties of C4H7NO2S).

Thiazolidine-4-carboxylic acid (cas: 444-27-9) belongs to thiazolidine derivatives. Thiazolidine motifs are very intriguing heterocyclic five-membered moieties present in diverse natural and bioactive compounds having sulfur at the first position and nitrogen at the third position. Thiazolidine-2,4-dione (TZD) is an important derivative of thiazolidine with a sulfur and nitrogen atom in positions 1 and 3, and carbonyl in position 4 of the ring. These derivatives have a wide range of medicinal applications such as antiviral, antimicrobial, anticonvulsant, antiinflammatory, and antimalarial activities.Computed Properties of C4H7NO2S

Referemce:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

Preparation of optically active 2-thiazolidinecarboxylic acid by asymmetric transformation was written by Shiraiwa, Tadashi;Katayama, Takashi;Ishikawa, Joji;Asai, Takeshi;Kurokawa, Hidemoto. And the article was included in Chemical & Pharmaceutical Bulletin in 1999.Application of 16310-13-7 This article mentions the following:

Cysteamine was condensed with glyoxylic acid monohydrate in a mixture of acetic acid and ethanol in the presence of (2R,3R)- or (2S,3S)-tartaric acid [(R)- or (S)-TA], as the resolving agent, to give the salt of (-)-2-thiazolidinecarboxylic acid [(-)-2-THC] with (R)-TA or the salt of (+)-2-THC with (S)-TA. Treatment of these salts with triethylamine in methanol afforded (-)- and (+)-2-THC, I and II resp. I and II were determined to be enantiopure forms by comparing their powder X-ray diffraction patterns with that of (RS)-2-THC. The absolute configurations of I and II were estimated based on molar rotations of (2R,4R)- and (2S,4R)-2,4-thiazolidinedicarboxylic acids, (R)-4-thiazolidinecarboxylic acid, and I and II. I was determined to have the (R)-configuration with II having the (S)-configuration. In the experiment, the researchers used many compounds, for example, Thiazolidine-2-carboxylic acid (cas: 16310-13-7Application of 16310-13-7).

Thiazolidine-2-carboxylic acid (cas: 16310-13-7) belongs to thiazolidine derivatives. Thiazolidine is an important scaffold and has a wide range of promising biological activities. Thiazolidine derivatives have reported anti-inflammatory and anti-nociceptive activity. In addition, the use of thiazolidines as an inhibitor of tyrosyl-DNA phosphodiesterase Iand influenza neuraminidase, pro-drugs for the treatment of cystinosis, radioprotective against γ-irradiation and as S1P1 receptor agonist has also been reported.Application of 16310-13-7

Referemce:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

Design and synthesis of new substituted spirooxindoles as potential inhibitors of the MDM2-p53 interaction was written by Barakat, Assem;Islam, Mohammad Shahidul;Ghawas, Hussien Mansur;Al-Majid, Abdullah Mohammed;El-Senduny, Fardous F.;Badria, Farid A.;Elshaier, Yaseen A. M. M.;Ghabbour, Hazem A.. And the article was included in Bioorganic Chemistry in 2019.Formula: C4H7NO2S This article mentions the following:

The designed compounds, 4a-p, were synthesized using a simple and smooth method with an asym. 1,3-dipolar reaction as the key step. The chem. structures for all synthesized compounds were elucidated and confirmed by spectral anal. The mol. complexity and the absolute stereochem. of 4b and 4e designed analogs were determined by X-ray crystallog. anal. The anticancer activities of the synthesized compounds were tested against colon (HCT-116), prostate (PC-3), and hepatocellular (HepG-2) cancer cell lines. Mol. modeling revealed that the compound 4d binds through hydrophobic-hydrophobic interactions with the essential amino acids (LEU: 57, GLY: 58, ILE: 61, and HIS: 96) in the p53-binding cleft, as a standard p53-MDM2 inhibitor (6SJ). The mechanism underlying the anticancer activity of compound 4d was further evaluated, and the study showed that compound 4d inhibited colony formation, cell migration, arrested cancer cell growth at G2/M, and induced apoptosis through intrinsic and extrinsic pathways. Transactivation of p53 was confirmed by flow cytometry, where compound 4d increased the level of activated p53 and induced mRNA levels of cell cycle inhibitor, p21. In the experiment, the researchers used many compounds, for example, Thiazolidine-4-carboxylic acid (cas: 444-27-9Formula: C4H7NO2S).

Thiazolidine-4-carboxylic acid (cas: 444-27-9) belongs to thiazolidine derivatives. Derivatives, thiazolidines, are known. For example, the drug pioglitazone contains a thiazolidine ring. Another drug that contains a thiazolidine ring is the antibiotic penicillin. Thiazolidine and its composites are key components of many natural products and drugs , and are also present in many synthetic compounds such as anticancer, anti-inflammatory, antitubercular, antifungal, antiviral, anti-HIV, cytotoxicity, antitrypanosomal, antinociceptive and anti-hypernociceptive compounds.Formula: C4H7NO2S

Referemce:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

Crystal structures of two triazola-dioxola-benzenacyclononaphanes was written by Viswanathan, Vijayan;Rao, Naga Siva;Raghunathan, Raghavachary;Velmurugan, Devadasan. And the article was included in Acta Crystallographica, Section E: Crystallographic Communications in 2015.Reference of 444-27-9 This article mentions the following:

In the title compounds, C₂₅H₂₉BrN₅O₇, (I) [systematic name: (Z)-1⁵-bromo-3²,3²-dimethyl-2¹-nitro-2²,2³,2⁵,2⁶,2⁷,2^7a,3^3a,3⁵,3⁶,3^6a-decahydro-2¹ H,6¹ H-4,9-dioxa-2(3,2)-pyrrolizina-6(4,1)-triazola-3(5,6)-furo[2,3-d][1,3]dioxola-1(1,2)-benzenacyclononaphane], and C₂₄H₂₉N₅O₇S, (II) [systematic name: (Z)-3²,3²-dimethyl-2⁷-nitro-2⁵,2⁶,2⁷,2^7a,3^3a,3⁵,3⁶,3^6a-octahydro-2¹ H,2³ H,6¹ H-4,9-dioxa-2(5,6)-pyrrolo[1,2-c]thiazola-6(4,1)-triazola-3(5,6)-furo[2,3-d][1,3]dioxola-1(1,2)-benzenacyclononaphane], the triazole rings adopt almost planar conformations. In (I), the fused pyrrolidine rings adopt envelope conformations with the C atoms opposite the fused N-C bond as the flap in each ring, and their mean planes are inclined to one another by 52.8 (3)°. In (II), the pyrrolidine and thiazole rings are both twisted on the fused N-C bond, and their mean planes are inclined to one another by 70.8 (2)°. In both (I) and (II), the furan ring adopts an envelope conformation with the adjacent C atom of the macrocycle as the flap. In the crystal of (I), mols. are linked via C-H···N and C-H···O hydrogen bonds, forming sheets parallel to (10-1), while in (II), mols. are linked via C-H···N and C-H···O hydrogen bonds, forming helical chains propagating along [010], which are linked via C-H···S hydrogen bonds, forming slabs parallel to (001). In the experiment, the researchers used many compounds, for example, Thiazolidine-4-carboxylic acid (cas: 444-27-9Reference of 444-27-9).

Thiazolidine-4-carboxylic acid (cas: 444-27-9) belongs to thiazolidine derivatives. Thiazolidine derivatives have been found to exhibit very prominent anti-inflammatory and anti-nociceptive activity. Open-chain compounds are obtained when thiazolidines are treated with tris(trimethylsilyl)silane in a reaction in which the thiazolidine derivatives act as a source of α-aminoalkyl radicals.Reference of 444-27-9

Referemce:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

Thioproline formation as a driver of formaldehyde toxicity in Escherichia coli was written by Patterson, Jenelle A.;He, Hai;Folz, Jacob S.;Li, Qiang;Wilson, Mark A.;Fiehn, Oliver;Bruner, Steven D.;Bar-Even, Arren;Hanson, Andrew D.. And the article was included in Biochemical Journal in 2020.Synthetic Route of C4H7NO2S This article mentions the following:

Formaldehyde (HCHO) is a reactive carbonyl compound that formylates and cross-links proteins, DNA, and small mols. It is of specific concern as a toxic intermediate in the design of engineered pathways involving methanol oxidation or formate reduction The interest in engineering these pathways is not, however, matched by engineering-relevant information on precisely why HCHO is toxic or on what damage-control mechanisms cells deploy to manage HCHO toxicity. The only well-defined mechanism for managing HCHO toxicity is formaldehyde dehydrogenase-mediated oxidation to formate, which is counterproductive if HCHO is a desired pathway intermediate. We therefore sought alternative HCHO damage-control mechanisms via comparative genomic anal. This anal. associated homologs of the Escherichia coli pepP gene with HCHO-related one-carbon metabolism Furthermore, deleting pepP increased the sensitivity of E. coli to supplied HCHO but not other carbonyl compounds PepP is a proline aminopeptidase that cleaves peptides of the general formula X-Pro-Y, yielding X + Pro-Y. HCHO is known to react spontaneously with cysteine to form the close proline analog thioproline (thiazolidine-4-carboxylate), which is incorporated into proteins and hence into proteolytic peptides. We therefore hypothesized that certain thioproline-containing peptides are toxic and that PepP cleaves these aberrant peptides. Supporting this hypothesis, PepP cleaved the model peptide Ala-thioproline-Ala as efficiently as Ala-Pro-Ala in vitro and in vivo, and deleting pepP increased sensitivity to supplied thioproline. Our data thus (i) provide biochem. genetic evidence that thioproline formation contributes substantially to HCHO toxicity and (ii) make PepP a candidate damage-control enzyme for engineered pathways having HCHO as an intermediate. In the experiment, the researchers used many compounds, for example, Thiazolidine-4-carboxylic acid (cas: 444-27-9Synthetic Route of C4H7NO2S).

Thiazolidine-4-carboxylic acid (cas: 444-27-9) belongs to thiazolidine derivatives. Derivatives, thiazolidines, are known. For example, the drug pioglitazone contains a thiazolidine ring. Another drug that contains a thiazolidine ring is the antibiotic penicillin. Thiazolidine and its composites are key components of many natural products and drugs , and are also present in many synthetic compounds such as anticancer, anti-inflammatory, antitubercular, antifungal, antiviral, anti-HIV, cytotoxicity, antitrypanosomal, antinociceptive and anti-hypernociceptive compounds.Synthetic Route of C4H7NO2S

Referemce:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

1,3-Dipolar cycloaddition reaction on carbohydrate template: Stereoselective synthesis of glyco-spiro-heterocycles was written by Prasanna, R.;Purushothaman, S.;Raghunathan, R.. And the article was included in Tetrahedron in 2020.Synthetic Route of C4H7NO2S This article mentions the following:

A simple and an efficient stereoselective synthesis of glyco-spiro-heterocycles has been accomplished via 1, 3-dipolar cycloaddition (1,3-DC) reaction. The azomethine ylide generated by decarboxylative condensation of N-alkylated α-amino acids with various diketones was trapped by sugar derived dipolarophiles to give glyco-spiro-heterocycles in good yield (72-94%). All the cycloadducts were well characterized by FT IR, NMR, HRMS and HPLC. The structures were established by 2D NMR. The regio- and stereochem. outcome of some of the cycloadducts were confirmed by a single crystal X-ray anal. Effect of various solvents on 1, 3 DC reaction was also studied. In the experiment, the researchers used many compounds, for example, Thiazolidine-4-carboxylic acid (cas: 444-27-9Synthetic Route of C4H7NO2S).

Thiazolidine-4-carboxylic acid (cas: 444-27-9) belongs to thiazolidine derivatives. Thiazolidine motifs are very intriguing heterocyclic five-membered moieties present in diverse natural and bioactive compounds having sulfur at the first position and nitrogen at the third position. In addition, the use of thiazolidines as an inhibitor of tyrosyl-DNA phosphodiesterase Iand influenza neuraminidase, pro-drugs for the treatment of cystinosis, radioprotective against γ-irradiation and as S1P1 receptor agonist has also been reported.Synthetic Route of C4H7NO2S

Referemce:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

Metabolomic analysis of diet-induced obese mice supplemented with eicosapentaenoic acid was written by Nishitani, Shigeki;Fukuhara, Atsunori;Jinno, Yasutaka;Kawano, Hiroyuki;Yano, Takashi;Otsuki, Michio;Shimomura, Iichiro. And the article was included in Experimental and Clinical Endocrinology & Diabetes in 2020.Electric Literature of C4H7NO2S This article mentions the following:

Eicosapentaenoic acid (EPA) is an omega-3 fatty acid with anti-inflammatory effects. To determine the effects of EPA on metabolic pathways in obese adipose tissues and liver, mice were fed normal chow diet (NCD), high-fat diet (HFD), or 3% EPA-containing high fat diet (HFD+EPA) for 8 wk. Metabolomic anal. was performed using epididymal adipose tissues (epi WAT) and liver. Metabolites that were specifically elevated in HFD+EPA, were assessed for their anti-inflammatory properties using RAW264.7 macrophage cells. Body and adipose tissue weights were significantly higher in HFD than NCD, and lower in HFD+EPA than HFD. Plasma insulin levels were significantly higher in HFD than NCD, and lower in HFD+EPA compared with HFD. Plasma monocyte chemotactic protein-1 (MCP-1) levels were higher in HFD than NCD, and tended to be lower in HFD+EPA than HFD. The levels of intermediate metabolites in the glycolytic pathways were lower in HFD compared with NCD and HFD+EPA in both epi WAT and liver, while intermediate metabolites of the TCA cycles were elevated in HFD and HFD+EPA compared with NCD in epi WAT. Among the metabolites in epi WAT, the levels of thiaproline, phenaceturic acid, and pipecolic acid were specifically elevated in HFD+EPA, but not in HFD or NCD. Treatment of RAW264.7 cells with thiaproline significantly ameliorated LPS-induced iNOS expression, while pipecolic acid inhibited LPS-induced IL-1β expression. These results suggest that EPA normalizes glycolytic pathway intermediates in both epi WAT and liver, and induces metabolites with anti-inflammatory properties. In the experiment, the researchers used many compounds, for example, Thiazolidine-4-carboxylic acid (cas: 444-27-9Electric Literature of C4H7NO2S).

Thiazolidine-4-carboxylic acid (cas: 444-27-9) belongs to thiazolidine derivatives. The thiazolidine ring is a cyclic N,S acetal, and most syntheses of perhydrothiazolo [3,2-a]pyridines construct the five-membered ring by condensation of aldehydes or ketones either as such or masked. Thiazolidines are also used in peptide and protein modification, protein chemical synthesis, as activators to innate immunity and also act as immunostimulating agents.Electric Literature of C4H7NO2S

Referemce:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

Diversity-oriented one-pot multicomponent synthesis of chromanone-based 3,3′-pyrrolidinyl-spirooxindoles via a 1,3-dipolar cycloaddition reaction was written by Yue, Jing;Chen, Shuang;Zuo, Xiong;Liu, Xiong-Li;Xu, Sheng-Wen;Zhou, Ying. And the article was included in Tetrahedron Letters in 2019.Product Details of 444-27-9 This article mentions the following:

A new methodol. was developed for the highly efficient one-pot multicomponent synthesis of chromanone-based 3,3′-pyrrolidinyl-spirooxindoles via a 1,3-dipolar cycloaddition reaction of chromones with azomethine ylides (thermally generated in situ from isatins and proline or thioproline). Another valuable application of this method was for the less reactive chromone through a carboxylic acid-activation and then decarboxylation strategy, which enabled diversity-oriented synthesis of complex pirooxindoles bearing four contiguous stereocenters (one of which is a spiro quaternary stereocenter) with high efficiency and stereoselectivity (up to 90% yield and 20:1 d.r.). This protocol could provide libraries of stereochem. rich and multiple pharmecore collections, that will help in search for new drug-like mols. In the experiment, the researchers used many compounds, for example, Thiazolidine-4-carboxylic acid (cas: 444-27-9Product Details of 444-27-9).

Thiazolidine-4-carboxylic acid (cas: 444-27-9) belongs to thiazolidine derivatives. Thiazolidines undergo hydrolysis to aldehyde and amino thiol under acid or basic aqueous conditions. Thiazolidines are also used in peptide and protein modification, protein chemical synthesis, as activators to innate immunity and also act as immunostimulating agents.Product Details of 444-27-9

Referemce:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

Metabolomics analysis of blood identifies potential biomarkers and possible treatment targets for nocturia was written by Kira, Satoru;Mitsui, Takahiko;Miyamoto, Tatsuya;Ihara, Tatsuya;Nakagomi, Hiroshi;Hashimoto, Yuka;Takamatsu, Hajime;Tanahashi, Masayuki;Takeda, Masahiro;Sawada, Norifumi;Takeda, Masayuki. And the article was included in Therapeutic Advances in Urology in 2019.Name: Thiazolidine-4-carboxylic acid This article mentions the following:

Background:: Our aim was to investigate the association between serum metabolites and nocturia. Methods:: A total of 66 males aged 65-80 years were enrolled in this study and stratified according to micturition behavior, which was characterized in terms of the 24 h frequency volume chart (FVC) for 3 consecutive days, the International Prostate Symptom Score (IPSS), and quality-of-life score. Between-group comparisons of metabolite levels employed the Welch t test. The relationship between nocturia and metabolite profiles was determined using multivariable logistic regression anal. Results:: Of 66 participants, 45 were included in the nocturia group and 21 in the control group. There were no differences in background factors between the two groups. FVC anal. revealed that urine production during night-time, as well as micturition frequency during daytime and night-time were significantly higher in the nocturia group. CE-TOFMS identified eight metabolites whose plasma levels differed between the two groups. Multivariate anal. indicated that increased levels of lauric acid and imidazolelactic acid, as well as decreased levels of thiaproline and glycerol, contribute to the etiol. of nocturia in aged men. Conclusions:: Our findings suggest that abnormal serum levels of metabolites in several pathways play a role in the pathogenesis of nocturia in aged men. In the experiment, the researchers used many compounds, for example, Thiazolidine-4-carboxylic acid (cas: 444-27-9Name: Thiazolidine-4-carboxylic acid).

Thiazolidine-4-carboxylic acid (cas: 444-27-9) belongs to thiazolidine derivatives. The thiazolidine ring is a cyclic N,S acetal, and most syntheses of perhydrothiazolo [3,2-a]pyridines construct the five-membered ring by condensation of aldehydes or ketones either as such or masked. Thiazolidine is prepared as it was in its first reported synthesis, by the condensation of cysteamine and formaldehyde. Other thiazolidines may be synthesized by similar condensations. A notable derivative is 4-carboxythiazolidine, derived from formaldehyde and cysteine.Name: Thiazolidine-4-carboxylic acid

Referemce:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

Assessment of the effects of repeated freeze thawing and extended bench top processing of plasma samples using untargeted metabolomics was written by Goodman, Kelli;Mitchell, Matthew;Evans, Anne M.;Miller, Luke A. D.;Ford, Lisa;Wittmann, Bryan;Kennedy, Adam D.;Toal, Douglas. And the article was included in Metabolomics in 2021.Reference of 444-27-9 This article mentions the following:

Introduction: Clin. metabolomics has utility as a screen for inborn errors of metabolism (IEM) and variant classification in patients with rare disease. It is important to understand and characterize preanal. factors that influence assay performance during patient sample testing. Objectives: To evaluate the impact of extended thawing of human EDTA plasma samples on ice prior to extraction as well as repeated freeze-thaw cycling of samples to identify compounds that are unstable prior to metabolomic anal. Twenty-four (24) donor EDTA plasma samples were collected and immediately frozen at – 80 °C. Twelve samples were thawed on ice and extracted for anal. at time 0, 2, 4, and 6 h. Twelve other donor samples were repeatedly thawed and frozen up to four times and analyzed at each cycle. Compound levels at each time point/freeze-thaw cycle were compared to the control samples using matched-paired t tests to identify analytes affected by each condition. We identified 1026 biochems. across all samples. Incubation of thawed EDTA plasma samples on ice for up to 6 h resulted in < 1% of biochems. changing significantly. Freeze-thaw cycles affected a greater percentage of the metabolome; ∼ 2% of biochems. changed after 3 freeze-thaw cycles. Our study highlights that the number and magnitude of these changes are not as widespread as other aspects of improper sample handling. In total, < 3% of the metabolome detected on our clin. metabolomics platform should be disqualified when multiple freeze-thaw cycles or extended thawing at 4 °C are performed on a given sample. In the experiment, the researchers used many compounds, for example, Thiazolidine-4-carboxylic acid (cas: 444-27-9Reference of 444-27-9).

Thiazolidine-4-carboxylic acid (cas: 444-27-9) belongs to thiazolidine derivatives. In the thiazolidine nucleus, a large number of substitutions are possible on 2, 4 and 5 positions responsible for enhancing the compound’s pharmaceutical importance. In addition, the use of thiazolidines as an inhibitor of tyrosyl-DNA phosphodiesterase Iand influenza neuraminidase, pro-drugs for the treatment of cystinosis, radioprotective against γ-irradiation and as S1P1 receptor agonist has also been reported.Reference of 444-27-9

Referemce:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com