10/9/2021 News Extended knowledge of Benzo[d]thiazole-2-carbonitrile

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Organic nitriles constitute key precursors and central intermediates in organic synthesis. In addition, nitriles represent a versatile motif found in numerous medicinally and biologically important compounds. Generally, these nitriles are synthesized by traditional cyanation procedures using toxic cyanides. Herein, we report the selective and environmentally benign oxidative conversion of primary amines for the synthesis of structurally diverse aromatic, aliphatic and heterocyclic nitriles using a reusable “nanorust” (nanoscale Fe2O3)-based catalysts applying molecular oxygen.

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Reference:
Thiazole | C3H7536NS – PubChem,
Thiazole | chemical compound | Britannica

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Invited for this month’s cover picture is the group of Dr. Yann Seimbille at the Life Sciences Division at TRIUMF (Canada). The cover picture shows how a simple and innovative methodology based on the bioorthogonal click reaction between 2-cyanobenzothiazole and 1,2-aminothiol has been elaborated to facilitate the labeling of peptide biovectors. Read the full text of their Communication at 10.1002/open.201700191.

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Thiazole | C3H7543NS – PubChem,
Thiazole | chemical compound | Britannica

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Arene and heteroarenediazonium o-benzenedisulfonimides can be used as efficient reagents in Sandmeyer cyanation. This work reports such reactions carried out by us under very mild conditions using tetrabutyl ammonium cyanide as a safe cyanide source and, interestingly, without the need for a Cu catalyst. The reactions have given rise to aryl nitriles in good yields (25 examples, average yield 75%). A good amount of o-benzenedisulfonimide was recovered from each reaction and then reused to prepare other salts. Mechanistic insights have allowed us to highlight the fundamental role of the o-benzenedisulfonimide anion as an electron transfer agent.

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Thiazole | C3H7555NS – PubChem,
Thiazole | chemical compound | Britannica

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This work describes the synthesis of a series of tricyclic lactones based on 4-hydroxy-1,3-thiazoles prepared by the classic Hantzsch synthesis. The tricyclic lactones are more rigid than the parent 4-hydroxythiazoles and are featured not only by fluorescence in solution, but also in the solid state. An extension of the chromophoric system was successfully realized by integration of the benzothiazole substructure, thus resulting in bathochromic shifts of absorption and also fluorescence. The new synthesized lactones additionally show interesting properties in solution, whereby the initial blue fluorescence changes dramatically with a variation of the pH value. Georg Thieme Verlag Stuttgart · New York.

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Thiazole | C3H7514NS – PubChem,
Thiazole | chemical compound | Britannica

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Liver tissue engineering is going to be an effective treatment for end-stage liver disease. In this work, we distributed bone marrow mesenchymal stem cells (BMSCs) into a fast-forming hydrogel system to develop a liver-mimicking construct for liver regeneration. The advantage of this hydrogel system was that this BMSC-encapsulating hydrogel could be formed via a bioorthogonal reaction between 2-cyanobenzothiazole and cysteine within several seconds. Thereafter, we explored the morphology, biocompatibility, and expressions of hepatic differentiation markers of this hydrogel system. These results illustrated that this system could provide a suitable niche for BMSC proliferation and differentiation, which could aid in future biomedical research of liver regeneration.

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Thiazole | C3H7541NS – PubChem,
Thiazole | chemical compound | Britannica

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The cyclization procedure of N-aryl iminodithiazoles into 2-cyanobenzothiazoles was re-investigated with the aim to develop original and environmentally friendly procedures. In this article, the benefits associated with the microwave methodology are reported and the opportunity to use solvent-free procedures in order to scale up organic synthesis is studied. The result obtained show that the strong thermal effects due to graphite/microwaves interaction can be efficiently used for the synthesis of heterocyclic molecules for which traditional methods failed or are less attractive.

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Reference:
Thiazole | C3H7526NS – PubChem,
Thiazole | chemical compound | Britannica

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Proteins constitute the majority of nature?s worker biomolecules. Designed for specific functions, complex tertiary structures make proteins ideal candidates for analysing natural systems and creating novel biological tools. Owing to both their large size and the need for proper folding, de novo synthesis of proteins has been quite a challenge, leading scientists to focus on modifying protein templates already provided by nature. Recently developed methods for protein modification fall into two broad categories: those that can modify the natural protein template directly and those that require genetic manipulation of the amino acid sequence before modification. The goal of this Review is not only to provide a window through which to view the many opportunities created by novel protein modification techniques? but also to act as an initial guide to help scientists find direction and form ideas in an ever-growing field. In addition to highlighting methods reported in the past 5 years, we aim to provide a broader sense of the goals and outcomes of protein modification and bioconjugation in general. While the main body of this paper comprises reactions involving the direct modification of expressed proteins, some further functionalization strategies as well as biological applications are also acknowledged. The discussion concludes by speculating which trends and discoveries will most likely come next in the field.

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Thiazole | C3H7534NS – PubChem,
Thiazole | chemical compound | Britannica

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Purpose: Positron emission tomography (PET) imaging of apoptosis is very important for early evaluation of tumor therapeutic efficacy. A stimuli-responsive probe based on the peptide sequence Asp-Glu-Val-Asp (DEVD), [18F]DEVD-Cys(StBu)-PPG(CBT)-AmBF3 ([18F]1), for PET imaging of tumor apoptosis was designed and prepared. This study aimed to develop a novel smart probe using a convenient radiosynthesis method and to fully examine the sensitivity and specificity of the probe response to the tumor treatment. Methods: The radiolabelling precursor DEVD-Cys(StBu)-PPG(CBT)-AmBF3 (1) was synthesized through multistep reactions. The reduction together with caspase-controlled macrocyclization and self-assembly of 1 was characterized and validated in vitro. After [18F]fluorination in the buffer (pH= 2.5), the radiolabelling yield (RLY), radiochemical purity (RCP) and stability of the probe [18F]1 in PBS and mouse serum were investigated by radio-HPLC. The sensitivity and specificity of [18F]1 for detecting the drug-induced apoptosis was fully evaluated in vitro and in vivo. The effect of cold precursor 1 on the cell uptake and tumor imaging of [18F]1 was also assessed. The level of activated caspase-3 in Hela cells and tumors with or without apoptosis induction was analyzed and compared by western blotting and histological staining. Results: The whole radiosynthesis process of [18F]1 was around 25 min with RLY of 50%, RCP of over 99% and specific activity of 1.45 ± 0.4 Ci/mumol. The probe was very stable in both PBS and mouse serum within 4 h. It can be activated by caspase-3 and then undergo an intermolecular cyclization to form nanosized particles. The retained [18F]1 in DOX-treated HeLa cells was 2.2 folds of that in untreated cells. Within 1 h microPET imaging of the untreated Hela-bearing mice, the injection of [18F]1 resulted in the increase of the uptake ratio of tumor to muscle (T/M) only from 1.74 to 2.18, while in the DOX-treated Hela-bearing mice T/M increased from 1.88 to 10.52 and the co-injection of [18F]1 and 1 even led to the increase of T/M from 3.08 to 14.81. Conclusions: A caspase-responsive smart PET probe [18F]1 was designed and prepared in a kit-like manner. Co-injection of [18F]1 and 1 generated remarkably enhanced tumor uptake and signal-to-noise ratio in the tumor-bearing mice with drug-induced apoptosis, which correlated well with the expression level of activated caspase-3. This early readout of treatment response ensured that the probe [18F]1 could serve as a promising PET imaging probe for timely and noninvasive evaluation of tumor therapy.

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Reference:
Thiazole | C3H7533NS – PubChem,
Thiazole | chemical compound | Britannica

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The synthetic route to and a preliminary biological evaluation of novel indolo[1,2-c]quinazolines (8) and benzimidazo[1,2-c]quinazolines (9) are described. The products were obtained by condensation of the appropriate diamines (e.g. 2-(2-aminophenyl)indole or 2-(2-aminophenyl)benzimidazole) with 2-cyanobenzothiazoles. This work further demonstrates the general applicability of microwaves for a facile and rapid access to original heterocycles with potential pharmaceutical value.

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Thiazole | C3H7519NS – PubChem,
Thiazole | chemical compound | Britannica

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Stimuli-responsive nanotheranostics based on lanthanide-doped upconversion nanoparticles for cancer imaging and therapy: current advances and future challenges

Theranostic nanoplatform integrated with concurrent diagnostic and therapeutic capabilities has attracted increasing attentions recently in the field of nanomedicine since it offers great opportunities in the fight against various major diseases, such as cancer. In recent years, lanthanide-doped upconvertion nanoparticles (UCNPs), have been explored for potential applications in cancer diagnostics and treatment owing to their unique merits such as enhancing penetration depths and minimizing background auto?uorescence, photo-bleaching as well as photodamage to biological specimens, and reducing adverse side effects of NIR triggered treatments. Of particular interest is to construct stimuli-responsive nanotheranostic platforms based on UCNPs that imaging and anticancer activities in response to various internal/external stimuli. In this review article, we would like to focus on the recent progress of UCNPs in their applications of stimuli-responsive theranostics that trigger the diagnostic and therapeutic functions in response to various stimuli, including near infrared (NIR) light, pH, glutathione (GSH), reactive oxygen species (ROS), enzyme, and temperature. Furthermore, the future directions and challenges in the development of UCNPs for stimuli-responsive theranostics are discussed.

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Reference:
Thiazole | C3H7518NS – PubChem,
Thiazole | chemical compound | Britannica