Heterocyclic Building Blocks-Thiazolidine

Inhibition of collagen production delays malignant mesothelioma tumor growth in a murine model was written by Abayasiriwardana, Keith S.;Wood, Michael K.;Prele, Cecilia M.;Birnie, Kimberly A.;Robinson, Bruce W.;Laurent, Geoffrey J.;McAnulty, Robin J.;Mutsaers, Steven E.. And the article was included in Biochemical and Biophysical Research Communications in 2019.Application of 444-27-9 This article mentions the following:

This study examined the effect of inhibiting collagen production on mesothelioma cell proliferation in vitro and tumor growth in vivo. Collagen production by mesothelioma cells was inhibited by incubating cells in vitro with the proline analog thiaproline (thiazolidine-4-carboxylic acid) or by oral administration of thiaproline in a murine tumor model. Cell cytotoxicity was measured using neutral red uptake and lactate dehydrogenase assays. Proliferation was measured by tritiated thymidine incorporation, and inflammatory cell influx, proliferation, apoptosis and angiogenesis in tumors examined by immunohistochem. labeling. Tumor size was determined by tumor weight and collagen production was measured by HPLC. Thiaproline at non-toxic doses significantly reduced basal and TGF-induced collagen production by over 50% and cell proliferation by over 65%. In vivo thiaproline administration inhibited tumor growth at 10 days, decreasing the median tumor weight by 80%. The mean concentration of collagen was 50% lower in the thiaproline-treated tumors compared with the controls. There were no significant differences in vasculature or inflammatory cell infiltration but apoptosis was increased in thiaproline treated tumors at day 10. In conclusion, these observations strongly support a role for collagen in mesothelioma growth and establish the potential for inhibitors of collagen synthesis in mesothelioma treatment. In the experiment, the researchers used many compounds, for example, Thiazolidine-4-carboxylic acid (cas: 444-27-9Application 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. 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.Application of 444-27-9

Referemce:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

The synthetic elicitor 2-(5-bromo-2-hydroxy-phenyl)-thiazolidine-4-carboxylic acid links plant immunity to hormesis was written by Rodriguez-Salus, Melinda;Bektas, Yasemin;Schroeder, Mercedes;Knoth, Colleen;Vu, Trang;Roberts, Philip;Kaloshian, Isgouhi;Eulgem, Thomas. And the article was included in Plant Physiology in 2016.Formula: C4H7NO2S This article mentions the following:

Here, we report on the characterization of one of these compounds, 2-(5-bromo-2-hydroxy-phenyl)-thiazolidine-4-carboxylic acid (BHTC). BHTC induces disease resistance of plants against bacterial, oomycete, and fungal pathogens and has a unique mode of action and structure. Surprisingly, we found that low doses of BHTC enhanced root growth in Arabidopsis, while high doses of this compound inhibited root growth, besides inducing defense. These effects are reminiscent of the hormetic response, which is characterized by low-dose stimulatory effects of a wide range of agents that are toxic or inhibitory at higher doses. Like its effects on defense, BHTC-induced hormesis in Arabidopsis roots is partially dependent on the WRKY70 transcription factor. Interestingly, BHTC-induced root hormesis is also affected in the auxin-response mutants axr1-3 and slr-1. By mRNA sequencing, we uncovered a dramatic difference between transcriptional profiles triggered by low and high doses of BHTC. Instead, low BHTC levels trigger a coordinated intercompartmental transcriptional response manifested in the suppression of photosynthesis- and respiration-related genes in the nucleus, chloroplasts, and mitochondria as well as the induction of development-related nuclear genes. Taken together, our functional characterization of BHTC links defense regulation to hormesis and provides a hypothetical transcriptional scenario for the induction of hormetic root growth. 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. Thiazolidine derivatives have been found to exhibit very prominent 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.Formula: C4H7NO2S

Referemce:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

Synthesis, Characterization, and Cytotoxicity of New Spirooxindoles Engrafted Furan Structural Motif as a Potential Anticancer Agent was written by Altowyan, Mezna Saleh;Soliman, Saied M.;Haukka, Matti;Al-Shaalan, Nora Hamad;Alkharboush, Aminah A.;Barakat, Assem. And the article was included in ACS Omega in 2022.Category: thiazolidine This article mentions the following:

A new series of spirooxindoles I [X = S, H₂C; R = 6-Cl, 5-O₂N; R¹ = 2-Cl, 4-Cl; R² = Br, O₂N], II [R³ = Br, O₂N] and III based on ethylene derivatives having furan aryl moiety were reported. The new hybrids I, II and III were achieved via [3 + 2] cycloaddition reaction as an economic one-step efficient approach. The final constructed spirooxindoles I, II and III have four contiguous asym. carbon centers. The structure of IV [R⁴ = Br, R⁵ = 4-Cl] was exclusively confirmed using X-ray single crystal diffraction. The supramol. structure of IV [R⁴ = Br, R⁵ = 4-Cl] was controlled by O···H, H···H, and C···C intermol. contacts. It includes layered mols. interconnected weak C-H···O (2.675 Å), H···H (2.269 Å), and relatively short Cl···Br interhalogen interactions [3.4500(11)Å]. Using Hirshfeld anal., the percentages of these intermol. contacts were 10.6, 25.7, 6.4, and 6.2%, resp. The spirooxindoles along with ethylene derivatives having furan aryl moiety were assessed against breast (MCF7) and liver (HepG2) cancer cell lines. The results indicated that the new chalcone IV [R⁴ = Br, R⁵ = 2-Cl] showed excellent activity in both cell lines (MCF7 and HepG2) with IC₅₀ = 4.1 ± 0.10μM/mL (MCF7) and 3.5 ± 0.07μM/mL (HepG2) compared to staurosporine with 4.3 and 2.92 folds. Spirooxindoles II [R³ = Br] (IC₅₀ = 4.3 ± 0.18μM/mL), I [X = S, R = 6-Cl, R¹ = 2-Cl, R² = Br] (IC₅₀ = 10.3 ± 0.40μM/mL), I [X = H₂C, R = 6-Cl, R¹ = 4-Cl, R² = O₂N] (IC₅₀ = 10.7 ± 0.38μM/mL), and II [R³ = O₂N] (IC₅₀ = 4.7 ± 0.18μM/mL) exhibited potential activity against breast adenocarcinoma, while compounds II [R³ = Br] (IC₅₀ = 6.9 ± 0.23μM/mL) and I [X = S, R = 6-Cl, R¹ = 2-Cl, R² = Br] (IC₅₀ = 3.5 ± 0.11μM/mL) were the most active hybrids against human liver cancer cell line (HepG2) compared to staurosporine [IC₅₀ = 17.8 ± 0.50μM/mL (MCF7) and 10.3 ± 0.23μM/mL (HepG2)]. Mol. docking study exhibited the virtual mechanism of binding of compound IV [R⁴ = Br, R⁵ = 2-Cl] as a dual inhibitor of EGFR/CDK-2 proteins, and this may highlight the mol. targets for its cytotoxic activity. In the experiment, the researchers used many compounds, for example, Thiazolidine-4-carboxylic acid (cas: 444-27-9Category: thiazolidine).

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.Category: thiazolidine

Referemce:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

Synthetic studies towards lagunamide C: Polyketide assembly investigations was written by Fatino, Anthony;Weese, Chelsea;Valdez, Salvador;Jimenez-Somarribas, Alberto;Rafferty, Ryan J.. And the article was included in Tetrahedron Letters in 2018.Application In Synthesis of (S)-4-Isopropylthiazolidine-2-thione This article mentions the following:

Lagunamide C is a depsipeptide natural product with low nM cytotoxicity towards numerous cancer cell lines. Synthetically, it is disconnected to a pentapeptide backbone and polyketide unit that possesses four stereogenic centers, of which two of centers are in question (C38 & 40). Our model system highlights a high-selective aldol addition via a Crimmin’s auxiliary setting the C40 ester linkage, and a non-facially selective cyclopropanation with subsequent ring opening for the installation of the C38 Me center. In the experiment, the researchers used many compounds, for example, (S)-4-Isopropylthiazolidine-2-thione (cas: 76186-04-4Application In Synthesis of (S)-4-Isopropylthiazolidine-2-thione).

(S)-4-Isopropylthiazolidine-2-thione (cas: 76186-04-4) belongs to thiazolidine derivatives. Thiazolidine derivatives have been found to exhibit very prominent anti-inflammatory and anti-nociceptive activity. 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.Application In Synthesis of (S)-4-Isopropylthiazolidine-2-thione

Referemce:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

Endogenous alkaloids in man. XXI. Analysis of glyoxylate-derived 1,3-thiazolidines and their precursors after trimethylsilylation by gas chromatography-mass spectrometry was written by Bringmann, Gerhard;Hesselmann, Christiana;Feineis, Doris. And the article was included in Journal of Chromatography A in 1995.Application of 16310-13-7 This article mentions the following:

A gas chromatog. procedure was developed for the simultaneous anal. of glyoxylate-derived 1,3-thiazolidines and their precursors, such as L-cysteine, cysteamine, and D-(-)-penicillamine as well as the toxic glyoxylic acid. The assay involves conversion of these highly polar compounds to volatile trimethylsilyl (TMS) derivatives, chromatog. on a polar fused-silica capillary column, and determination using flame-ionization detection or electron-impact ionization mass spectrometry. On the basis of this anal. device, the resolution of the diastereomeric pairs of 1,3-thiazolidine-2,4-dicarboxylic acids was achieved. Based upon the observation that no epimerization occurs during the silylation procedure, for the first time a reliable method was established for the determination of the diastereomeric ratio of such alkaloid-type heterocycles on a trace scale. Furthermore, studies concerning thiazolidine formation under derivatization conditions in the presence of the precursors glyoxylic acid and D-(-)-penicillamine are described. 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 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. Thiazolidines have been applied as prodrug derivatives for various steroids containing a 3-carbonyl group to improve their topical anti-inflammatory activity. Application of 16310-13-7

Referemce:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

Total synthesis and structural validation of cyclodepsipeptides solonamide A and B was written by Kitir, Betul;Baldry, Mara;Ingmer, Hanne;Olsen, Christian A.. And the article was included in Tetrahedron in 2014.Reference of 110199-17-2 This article mentions the following:

Microorganisms are an attractive source of new natural products with antimicrobial properties, and the marine environment constitutes a prolific resource of bioactive microorganisms. During a global research expedition (Galathea III), two depsipeptides, solonamide A and solonamide B, were isolated from the marine bacterium Photobacterium halotolerance and were found to inhibit virulence gene expression in the serious human pathogen, Staphylococcus aureus. They act by interfering with the agr quorum sensing system and show resemblance to the endogenous S. aureus quorum sensing peptide, autoinducing peptide I (AIP-I). To enable more comprehensive studies, we embarked on the chem. synthesis of solonamides A and B. The key synthetic steps were formation of the (R)-β-hydroxy-fatty-acids by stereoselective aldol reactions and a cyclative macrolactamization, which proceeded under highly dilute conditions. Thus, the first total syntheses of the solonamides corroborated the originally assigned structures, and by changing the stereochem. of the auxiliary in the aldol steps we gained access to the natural products as well as their β³-epimers. In the experiment, the researchers used many compounds, for example, (R)-4-Benzylthiazolidine-2-thione (cas: 110199-17-2Reference of 110199-17-2).

(R)-4-Benzylthiazolidine-2-thione (cas: 110199-17-2) belongs to thiazolidine derivatives. Thiazolidines undergo hydrolysis to aldehyde and amino thiol under acid or basic aqueous conditions. 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.Reference of 110199-17-2

Referemce:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

Effects of wild zooplankton versus enriched rotifers and Artemia on the biochemical composition of Atlantic cod (Gadus morhua) larvae was written by Rocha, Giseli Swerts;Katan, Tomer;Parrish, Christopher C.;Kurt Gamperl, A.. And the article was included in Aquaculture in 2017.Computed Properties of C4H7NO2S This article mentions the following:

Diet at start feeding can affect fish development, pigmentation and growth, and live feed can provide all the dietary requirements of larvae. Enriched rotifers and Artemia are normally used as live feed in the first stages of com. larval production, however, wild zooplankton or copepods provide better results. The goal of this study was to evaluate whether supplementing enriched rotifers and Artemia (RA) with fish protein hydrolyzate (RA-PH) or a small amount of wild zooplankton (RA-Zoo; 5-10% of total prey items) would improve the nutritional quality of larval cod (Gadus morhua), and how it correlated with larval growth rates. Wild zooplankton had significantly higher proportions of the polyunsaturated fatty acids 22:6ω3 (DHA, 23%) and 20:5ω3 (EPA, 11%). Larvae fed wild zooplankton also had higher proportions of essential omega-3 fatty acids (43% RA-Zoo; ≈ 39-40% RA/RA-PH) and much higher EPA/ARA ratios compared to those only fed with enriched rotifers and Artemia or these prey items plus protein hydrolyzate (≈ 4 RA-Zoo; ≈ 1.3-3 RA/RA-PH). Further, these fatty acid proportions correlated significantly with larval growth rates and improved fish development. Based on these results, we recommend the inclusion of small amounts of wild zooplankton or com. produced copepods with high proportions of DHA and EPA, and low proportions of ARA, in the initial diet of Atlantic cod larvae. 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 is an important scaffold and has a wide range of promising biological activities. Thiazolidine derivatives have reported 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.Computed Properties of C4H7NO2S

Referemce:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

6′-(3-Bromophenyl)-7′-nitro-1′,6′,7′,7a′-tetrahydro-3′H-spiro[indeno[1,2-b]quinoxaline-11,5′-pyrrolo[1,2-c]thiazole] was written by Muthuselvi, C.;Muthu, M.;Athimoolam, S.;Ravikumar, B.;Pandiarajan, S.;Krishnakumar, R. V.. And the article was included in IUCrData in 2018.Safety of Thiazolidine-4-carboxylic acid This article mentions the following:

The title compound, C₂₆H₁₉BrN₄O₂S, crystallizes in a monoclinic C-centered lattice with eight mols. in the unit cell. The five-membered thiazole and pyrrolidine rings adopt envelope conformations and the bromophenyl and indenoquinoxaline planes are oriented at a dihedral angle of 61.6 (1)° to each other. The mol. structure features an intramol. C-H···N interaction leading to an S(6) ring motif. C(9) and C(10) chains along the c- and b-axis directions form through C-H···Br and C-H···S contacts, resp. In addition, C-H···O and C-H···N hydrogen bonds form inversion dimers with R²₂(10) and R²₂(14) motifs, resp. One O atom is disordered over two positions (occupancy ratio 0.63:0.37). In the experiment, the researchers used many compounds, for example, Thiazolidine-4-carboxylic acid (cas: 444-27-9Safety of Thiazolidine-4-carboxylic acid).

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. 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.Safety of Thiazolidine-4-carboxylic acid

Referemce:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

N-Propargylglycine: a unique suicide inhibitor of proline dehydrogenase with anticancer activity and brain-enhancing mitohormesis properties was written by Scott, Gary K.;Mahoney, Sophia;Scott, Madeleine;Loureiro, Ashley;Lopez-Ramirez, Alejandro;Tanner, John J.;Ellerby, Lisa M.;Benz, Christopher C.. And the article was included in Amino Acids in 2021.Application of 16310-13-7 This article mentions the following:

Proline dehydrogenase (PRODH) is a mitochondrial inner membrane flavoprotein critical for cancer cell survival under stress conditions and newly recognized as a potential target for cancer drug development. Reversible (competitive) and irreversible (suicide) inhibitors of PRODH have been shown in vivo to inhibit cancer cell growth with excellent host tolerance. Surprisingly, the PRODH suicide inhibitor N-propargylglycine (N-PPG) also induces rapid decay of PRODH with concordant upregulation of mitochondrial chaperones (HSP-60, GRP-75) and the inner membrane protease YME1L1, signifying activation of the mitochondrial unfolded protein response (UPR^mt) independent of anticancer activity. The present study was undertaken to address two aims: (i) use PRODH overexpressing human cancer cells (ZR-75-1) to confrm the UPR^mt inducing properties of N-PPG relative to another equipotent irreversible PRODH inhibitor, thiazolidine-2-carboxylate (T2C); and (ii) employ biochem. and transcriptomic approaches to determine if orally administered N-PPG can penetrate the blood-brain barrier, essential for its future use as a brain cancer therapeutic, and also potentially protect normal brain tissue by inducing mitohormesis. Oral daily treatments of N-PPG produced a dose-dependent decline in brain mitochondrial PRODH protein without detectable impairment in mouse health; furthermore, mice repeatedly dosed with 50 mg/kg N-PPG showed increased brain expression of the mitohormesis associated protease, YME1L1. Whole brain transcriptome (RNAseq) analyses of these mice revealed signifcant gene set enrichment in N-PPG stimulated neural processes (FDR p<0.05). Given this in vivo evidence of brain bioavailability and neural mitohormesis induction, N-PPG appears to be unique among anticancer agents and should be evaluated for repurposing as a pharmaceutical capable of mitigating the proteotoxic mechanisms driving neurodegenerative disorders. 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. 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.Application of 16310-13-7

Referemce:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

Multicomponent Dipolar Cycloaddition Strategy: Combinatorial Synthesis of Novel Spiro-Tethered Pyrazolo[3,4-b]quinoline Hybrid Heterocycles was written by Sumesh, Remani Vasudevan;Muthu, Muthumani;Almansour, Abdulrahman I.;Suresh Kumar, Raju;Arumugam, Natarajan;Athimoolam, S.;Jeya Yasmi Prabha, E. Arockia;Kumar, Raju Ranjith. And the article was included in ACS Combinatorial Science in 2016.HPLC of Formula: 444-27-9 This article mentions the following:

The stereoselective syntheses of a library of novel spiro-tethered pyrazolo[3,4-b]quinoline-pyrrolidine/pyrrolothiazole/indolizine-oxindole/acenaphthene hybrid heterocycles have been achieved through the 1,3-dipolar cycloaddition of azomethine ylides generated in situ from α-amino acids and 1,2-diketones to dipolarophiles derived from pyrazolo[3,4-b]quinoline derivatives In the experiment, the researchers used many compounds, for example, Thiazolidine-4-carboxylic acid (cas: 444-27-9HPLC of Formula: 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. Thiazolidines are also used in peptide and protein modification, protein chemical synthesis, as activators to innate immunity and also act as immunostimulating agents.HPLC of Formula: 444-27-9

Referemce:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com