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Chemical Structure| 2564-83-2 Chemical Structure| 2564-83-2

Structure of Tempo
CAS No.: 2564-83-2

Chemical Structure| 2564-83-2

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Tempo is a classic nitroxide radical and is a selective scavenger of mitochondrial ROS that dismutases superoxide in the catalytic cycle. Tempo induces DNA-strand breakage. Tempo can be used as an organocatalyst for the oxidation of primary alcohols to aldehydes. Tempo has mutagenic and antioxidant effects.

4.5 *For Research Use Only !

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Product Citations

Product Citations      Show More

Semenya, Julius ; Yang, Yuanjie ; Lee, Hye Joon ; Giannantonio, Kimberly A ; Manduva, Rikhil ; Picazo, Elias

Abstract: Carbon-heteroatom bonds are of great importance due to their prevalence in pharmaceuticals, agrochemicals, materials, and natural products. Despite the effective use of metal-catalyzed crosscoupling reactions between sp2-hybridized organohalides and soft heteroatomic nucleophiles for carbon-heteroatom bond formation, the use of sp3-hybridized organohalides remain limited and the coupling with remains elusive. Here, we report the coupling of sp3-hybridized benzyl or tertiary halides with soft thiol nucleophiles catalyzed by iron and extend the utility to alcohol and amine nucleophiles. The reaction is broad in substrate scope for both coupling partners and applicable in the construction of congested tri- and tetrasubstituted carbon centers as well as β-quaternary heteroatomic products. The synthetic utility is further emphasized by gram-scale synthesis and rapid herbicide library synthesis. Overall, we provide an efficient method to prepare pharmaceutically and materially relevant carbon-heteroatom bonds by expanding iron-catalyzed cross-coupling reactions to the coupling of sp3-hybridized organohalides with soft nucleophiles.

Boley, Alexander Joseph ;

Abstract: The selective and facile functionalization of C-H bonds - the most abundant bonds in all chemical space - remains a key driving factor for innovation in modern chemistry. Chapter 1 provides an overview of C-H functionalization research and its importance; discussion of C-H functionalization necessitates an analysis of subjects such as organometallic chemistry, radical generation and functionalization, and the synthetic benefits and challenges presented therein. Intersecting with discussion of C-H functionalization and radical chemistry, photoredox catalysis has played a major role in modern C-H functionalization methodologies, and as such is discussed in detail. Distinct and impactful C-H functionalization works from the Nicewicz lab are explored, providing a basis for the exploratory photoredox catalysis chemistry discussed in subsequent chapters. Chapter 2 explores attempts at generating and functionalizing azaallyl radical species via organic photoredox catalysis. Using the extreme oxidizing power of acridinium photoredox catalysts for novel modes of C-H functionalization circumvents the typically harsh conditions needed for azaallyl radical formation. While methods for α-amino functionalization are abundant, azaallyl radicals are uniquely long-lived, allowing for radical cascade and cyclization reactivity. While some success was afforded C-H functionalization with typical radical traps, control of the reactivity remains tenuous and the desired cascade-like cyclization remains elusive. Chapter 3 details a completed C-H functionalization methodology for the programmable synthesis of decorated piperazine cores via organic photoredox catalysis. The synthetic and medicinal importance piperazines is highlighted, as are the typical shortcomings of both traditional and state-of-the-art approaches for their synthesis. Optimization and scope of the cyclization reaction are explored in depth, and a complementary hydroamination strategy for the synthesis of complex diamine backbones from enecarbamates via organic photoredox catalysis is demonstrated. Chapter 4 serves as a conceptual successor to the piperazine methodology, establishing the foundation of a synthetic approach for an organic photoredox-catalyzed morpholine synthesis via a C-H functionalization strategy. Initial optimization of the desired reactivity is detailed in full, exploring somewhat divergent results based on seemingly innocuous changes to the reaction system. While the yield in either iteration of the model system remains low, significant options for future optimization remain in terms of catalyst choice and substrate design.

Purchased from AmBeed: ;

Fischer, Thomas ; Frasson, David ; Sievers, Martin ; Riedl, Rainer ;

Abstract: The severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) papain-like cysteine protease (PLpro) represents one of only two essential cysteine proteases involved in the regulation of viral replication. It, therefore, qualifies as a promising therapeutic target for the development of antiviral agents. We identified a previously synthesized protease inhibitor, resulting from an earlier project, as a PLpro inhibitor and crafted a structure-activity relationship around the hit, leading to the more potent inhibitors ZHAWOC6941 (17h) and ZHAWOC25153 (17o) displaying IC50 values of 8 and 7 µM, respectively. The two compounds represent a new class of PLpro inhibitors and, with single‐digit micromolar IC50 values, are comparable to inhibitors found in the literature.

Keywords: Inhibitor ; papain-like protease ; SARS-CoV-2 ; structure-activity relationship

Purchased from AmBeed: ; ; ;

Lim, Taeho ; Ryoo, Jeong Yup ; Han, Min Su ;

Abstract: In this study, we developed a simple transition-metal-free borylation reaction of aryl bromides. Bis-boronic acid (BBA), was used, and the borylation reaction was performed using a simple procedure at a mild temperature. Under mild conditions, aryl bromides were converted to arylboronic acids directly without any deprotection steps and purified by conversion to trifluoroborate salts. The functional group tolerance was considerably high. The mechanism study suggested that this borylation reaction proceeds via a radical pathway.

Alternative Products

Product Details of Tempo

CAS No. :2564-83-2
Formula : C9H18NO
M.W : 156.25
SMILES Code : CC1(C)CCCC(C)(C)N1[O]
MDL No. :MFCD00009599
InChI Key :QYTDEUPAUMOIOP-UHFFFAOYSA-N
Pubchem ID :2724126

Safety of Tempo

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H314
Precautionary Statements:P280-P305+P351+P338-P310
Class:8
UN#:3263
Packing Group:

Isoform Comparison

Biological Activity

In Vitro:

Cell Line
Concentration Treated Time Description References
Adult mouse cardiomyocytes 25 nmol/l 24 hours High glucose-induced mitochondrial superoxide generation and cell death were inhibited by mito-TEMPO Free Radic Biol Med. 2016 Jan;90:12-23.

In Vivo:

Species
Animal Model
Administration Dosage Frequency Description References
Mice Streptozotocin-induced type-1 diabetic mice and db/db mice Intraperitoneal injection 0.7 mg/kg/day Once daily for 30 days Mito-TEMPO inhibited mitochondrial ROS generation, reduced myocardial hypertrophy and apoptosis, and improved myocardial function Free Radic Biol Med. 2016 Jan;90:12-23.
C57BL/6J mice Acetaminophen (APAP) hepatotoxicity model Intraperitoneal injection 10 or 20 mg/kg Single dose, evaluated 1.5 hours later To evaluate the protective effect of Mito-Tempo against APAP hepatotoxicity. Results showed that Mito-Tempo dose-dependently attenuated liver injury, reduced necrotic areas, decreased ALT activity, and mitigated mitochondrial oxidant stress and dysfunction. Arch Toxicol. 2017 Feb;91(2):761-773

Protocol

Bio Calculators
Preparing Stock Solutions 1mg 5mg 10mg

1 mM

5 mM

10 mM

6.40mL

1.28mL

0.64mL

32.00mL

6.40mL

3.20mL

64.00mL

12.80mL

6.40mL

Dissolving Methods
Please choose the appropriate dissolution scheme according to your animal administration guide.For the following dissolution schemes, clear stock solution should be prepared according to in vitro experiments, and then cosolvent should be added in turn:

in order to ensure the reliability of the experimental results, the clarified stock solution can be properly preserved according to the storage conditions; The working fluid for in vivo experiment is recommended to be prepared now and used on the same day;

The percentage shown in front of the following solvent refers to the volume ratio of the solvent in the final solution; If precipitation or precipitation occurs in the preparation process, it can be assisted by heating and/or ultrasound.
Protocol 1
Protocol 2

References

 

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