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2-Nitrobenzenesulfonic acid hydrazide, with the molecular formula C6H7N3O6S, is a hydrazide derivative of 2-nitrobenzenesulfonic acid. It is a white to light yellow crystalline powder that is soluble in water. This chemical compound is commonly used as a reagent in organic synthesis and is known for its anti-tumor and anti-fibrotic activities, making it a promising candidate for therapeutic applications in various areas.

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  • 5906-99-0 Structure
  • Basic information

    1. Product Name: 2-Nitrobenzenesulfonic acid hydrazide
    2. Synonyms: 2-Nitrobenzenesulfonic acid hydrazide;2-Nitrobenzenesulfonohydrazide;o-Nitrobenzenesulfonylhydrazide
    3. CAS NO:5906-99-0
    4. Molecular Formula: C6H7N3O4S
    5. Molecular Weight: 217.2
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 5906-99-0.mol
  • Chemical Properties

    1. Melting Point: 101 °C (decomp)
    2. Boiling Point: 432.3±47.0 °C(Predicted)
    3. Flash Point: N/A
    4. Appearance: /
    5. Density: 1.562±0.06 g/cm3(Predicted)
    6. Refractive Index: N/A
    7. Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
    8. Solubility: Acetonitrile (Slightly)
    9. PKA: 8.47±0.10(Predicted)
    10. Stability: Hygroscopic
    11. CAS DataBase Reference: 2-Nitrobenzenesulfonic acid hydrazide(CAS DataBase Reference)
    12. NIST Chemistry Reference: 2-Nitrobenzenesulfonic acid hydrazide(5906-99-0)
    13. EPA Substance Registry System: 2-Nitrobenzenesulfonic acid hydrazide(5906-99-0)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 5906-99-0(Hazardous Substances Data)

5906-99-0 Usage

Uses

Used in Organic Synthesis:
2-Nitrobenzenesulfonic acid hydrazide is used as a reagent in organic synthesis for its ability to facilitate various chemical reactions and the formation of new compounds.
Used in Production of Azo Dyes:
In the dye industry, 2-Nitrobenzenesulfonic acid hydrazide is used as a key component in the production of azo dyes, which are widely used for coloring fabrics, plastics, and other materials.
Used in Analytical Chemistry:
2-Nitrobenzenesulfonic acid hydrazide is used as a reagent for the determination of traces of aluminum, playing a crucial role in analytical chemistry for accurate and sensitive detection of aluminum in various samples.
Used in Pharmaceutical Research:
Due to its anti-tumor and anti-fibrotic activities, 2-Nitrobenzenesulfonic acid hydrazide is used in pharmaceutical research as a potential therapeutic agent for the development of treatments for cancer and fibrotic diseases.
Used in Drug Development:
2-Nitrobenzenesulfonic acid hydrazide is employed in drug development as a lead compound for the discovery and optimization of new drugs targeting tumor growth and fibrosis, aiming to improve patient outcomes and address unmet medical needs.

Check Digit Verification of cas no

The CAS Registry Mumber 5906-99-0 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,9,0 and 6 respectively; the second part has 2 digits, 9 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 5906-99:
(6*5)+(5*9)+(4*0)+(3*6)+(2*9)+(1*9)=120
120 % 10 = 0
So 5906-99-0 is a valid CAS Registry Number.

5906-99-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-Nitrobenzenesulfonohydrazide

1.2 Other means of identification

Product number -
Other names o-nitrophenylsulfonyl hydrazide

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:5906-99-0 SDS

5906-99-0Relevant articles and documents

Synthesis of alkaloid (-)-205b via stereoselective reductive cross-coupling and intramolecular [3+2] cycloaddition

Yang, Dexi,Micalizio, Glenn C.

, p. 15237 - 15240 (2012)

An asymmetric synthesis of alkaloid (-)-205B, a tricyclic member of the architecturally diverse family of natural products isolated from the skin of neotropical poison frogs, is described that proceeds through two recently developed stereoselective synthetic methods: (1) Ti-mediated allylic alcohol-imine reductive cross-coupling and (2) intramolecular [3+2] cycloaddition of a glyoxylate-based homoallylic nitrone. The utility of this latter cycloaddition process for the assembly of the stereochemically dense piperidine core of 205B is noteworthy, as this method enables direct [3+2] cycloaddition of an intermediate homoallylic (E)-nitrone via a pathway that is stereochemically unscathed by competitive [3,3]-sigmatropic rearrangement processes. Overall, the synthesis is asymmetric, concise, and highly stereoselective-features which point to the potential future utility of these chemical methods in natural product synthesis and medicinal chemistry.

A Synthetic Route to the Core Structure of (-)-Retigeranic Acid A

Wang, Xiao,Li, Dian,Zhang, Junlin,Gong, Jianxian,Fu, Junkai,Yang, Zhen

supporting information, p. 5092 - 5097 (2021/07/19)

Retigeranic acid A is a uniquely structured pentacyclic sesterterpene bearing eight stereogenic centers. We report a concise route to the core structure of (-)-retigeranic acid A. The stereochemistry of its six chiral centers and three quaternary carbon centers was well-controlled. This route features two intramolecular Pauson-Khand reactions (IMPKRs): the first forged the D and E rings to deliver the triquinane subunit, and the second constructed the A and B rings and diastereoselectively installed the quaternary C6a center.

Synthesis of benzimidazole derivatives as potent inhibitors for α-amylase and their molecular docking study in management of type-II diabetes

Hussain, Shafqat,Taha, Muhammad,Rahim, Fazal,Hayat, Shawkat,Zaman, Khalid,Iqbal, Naveed,Selvaraj, Manikandan,Sajid, Muhammad,Bangesh, Masroor Ahmad,Khan, Fahad,Khan, Khalid Mohammed,Uddin, Nizam,Shah, Syed Adnan Ali,Ali, Muhammad

, (2021/02/21)

In the search of potent α-amylase inhibitors, we have synthesized seventeen derivatives of 2-mercaptobenzimidazole bearing sulfonamide (1–17) and evaluated for their α-amylase inhibitory potential. All synthesized compounds display a variable degree of α-amylase activity having IC50 values ranging between 0.90 ± 0.05 to 11.20 ± 0.30 μM when compared with the standard drug acarbose having IC50 value 1.70 ± 0.10 μM. Compound 1, 2, 11, 12 and 14 having IC50 values 1.40 ± 0.10, 1.30 ± 0.05, 0.90 ± 0.05, 1.60 ± 0.05 and 1.60 ± 0.10 μM respectively were found many folds better than the standard drug acarbose. While others derivatives of the series showed good inhibitory potentials. All the synthesized compounds were characterized by HREI-MS, 1H and 13C NMR spectroscopy. Structure activity relationship (SAR) has been established for all newly synthesized analogs. Binding interactions between ligands and active residues of the enzyme were confirmed through molecular docking study.

Small molecule-mediated induction of endoplasmic reticulum stress in cancer cells

Basu, Sudipta,Biswas, Ankur,Lahiri, Mayurika,Pandey, Shalini,Sharma, Virender Kumar

supporting information, p. 1604 - 1611 (2021/10/23)

The endoplasmic reticulum (ER) is one of the crucial sub-cellular organelles controlling myriads of functions including protein biosynthesis, folding, misfolding and unfolding. As a result, dysregulation of these pathways in the ER is implicated in cancer development and progression. Subsequently, targeting the ER in cancer cells emerged as an interesting unorthodox strategy in next-generation anticancer therapy. However, development of small molecules to selectively target the ER for cancer therapy remained elusive and unexplored. To address this, herein, we have developed a novel small molecule library of sulfonylhydrazide-hydrazones through a short and concise chemical synthetic strategy. We identified a fluorescent small molecule that localized into the endoplasmic reticulum (ER) of HeLa cells, induced ER stress followed by triggering autophagy which was subsequently inhibited by chloroquine (autophagy inhibitor) to initiate apoptosis. This small molecule showed remarkable cancer cell killing efficacy in different cancer cells as mono and combination therapy with chloroquine, thus opening a new direction to illuminate ER-biology towards the development of novel anticancer therapeutics.

Synthesis, in vitro α-amylase inhibitory, and radicals (DPPH & ABTS) scavenging potentials of new N-sulfonohydrazide substituted indazoles

Rafique, Rafaila,Khan, Khalid Mohammed,Arshia,Chigurupati, Sridevi,Wadood, Abdul,Rehman, Ashfaq Ur,Salar, Uzma,Venugopal, Vijayan,Shamim, Shahbaz,Taha, Muhammad,Perveen, Shahnaz

, (2019/11/26)

Over-expression of α-amylase enzyme causes hyperglycemia which lead to many physiological complications including oxidative stress, one of the most commonly associated problem with diabetes mellitus. Marketed α-amylase inhibitors such as acarbose, voglibose, and miglitol used to treat type-II diabetes mellitus, but also linked to several harmful effects. Therefore, it is essential to explore new and nontoxic antidiabetic agents with additional antioxidant properties. In this connection, a series of new N-sulfonohydrazide substituted indazoles 1–19 were synthesized by multistep reaction scheme and assessed for in vitro α-amylase inhibitory and radical (DPPH and ABTS) scavenging properties. All compounds were fully characterized by different spectroscopic techniques including 1H, 13C NMR, EI-MS, HREI-MS, ESI-MS, and HRESI-MS. Compounds showed promising α-amylase inhibitory activities (IC50 = 1.23 ± 0.06–4.5 ± 0.03 μM) as compared to the standard acarbose (IC50 1.20 ± 0.09 μM). In addition to that all derivatives were found good to moderate scavengers of DPPH (IC50 2.01 ± 0.13–5.3 ± 0.11) and ABTS (IC50 = 2.34 ± 0.07–5.5 ± 0.07 μM) radicals, in comparison with standard ascorbic acid having scavenging activities with IC50 = 1.99 ± 0.09 μM, and IC50 2.03 ± 0.11 μM for DPPH and ABTS radicals. In silico molecular docking study was conducted to rationalize the binding interaction of α-amylase enzyme with ligands. Compounds were observed as mixed type inhibitors in enzyme kinetic characterization.

TRANSGLUTAMINASE 2 (TG2) INHIBITORS

-

Paragraph 00548, (2020/03/02)

Described herein are compounds and pharmaceutical compositions containing such compounds which inhibit transglutaminase 2 (TG2). Also described herein are methods for using such TG2 inhibitors, alone or in combination with other compounds, for treating diseases or conditions that would benefit from TG2 inhibition.

IRE1 SMALL MOLECULE INHIBITORS

-

Paragraph 00256, (2020/07/05)

Provided herein are small molecule inhibitors for the targeting or IRE1 protein family members. Binding may be direct or indirect. Further provided herein are methods of using IRE1 small molecule inhibitors for use in treating or ameliorating cancer in a subject. Moreover, IRE1 small molecule inhibitors described herein are for the treatment of cancer, where the cancer is a solid or hematologic cancer.

Total Syntheses of Disorazoles A1 and B1 and Full Structural Elucidation of Disorazole B1

Nicolaou,Bellavance, Gabriel,Buchman, Marek,Pulukuri, Kiran Kumar

supporting information, p. 15636 - 15639 (2017/11/14)

Described herein are the first total syntheses of naturally occurring antitumor agents disorazoles A1 and B1 and the full structural assignment of the latter. The syntheses were achieved through convergent strategies employing enantioselective constructions of the required building blocks, including a novel Sharpless epoxidation/enzymatic kinetic resolution of stannane-containing substrates that led selectively to both enantiomeric forms of an epoxy vinyl stannane, and a series of coupling reactions, including a Wittig reaction, a Suzuki coupling, a Stille coupling, a Yamaguchi esterification and a Yamaguchi macrolactonization.

Preparation method of mild diazomethane derivative

-

Paragraph 0110; 0111; 0119, (2017/08/28)

The invention discloses a preparation method of a mild diazomethane derivative. The preparation method comprises that EWG-substituted benzene sulfonyl chloride and hydrazine hydrate undergo a reaction to produce EWG-substituted benzene sulfonyl chloride, the EWG-substituted benzene sulfonyl chloride and aldehyde or ketone undergo a reaction to produce EWG-substituted benzenesulfonylhydrazone, and the EWG-substituted benzenesulfonylhydrazone, a base and an organic solvent are mixed and undergo a replacement reaction to produce a diazomethane derivative. The diazomethane derivative is not separated and purified and is further used for a tension small ring synthesis reaction and an insertion reaction. The benzene ring of benzenesulfonylhydrazone is introduced with an electron-withdrawing group EWG, and through electron effects and steric hindrance effects, the benzenesulfonyl group on the benzenesulfonylhydrazone is easily separated so that a diazomethane derivative is produced under very mild conditions and especially at the room temperature.

Copper-catalyzed: S -methylation of sulfonyl hydrazides with TBHP for the synthesis of methyl sulfones in water

Yang, Yu,Bao, Yajie,Guan, Qianqian,Sun, Qi,Zha, Zhenggen,Wang, Zhiyong

supporting information, p. 112 - 116 (2017/08/15)

A copper-catalyzed S-methylation of sulfonyl hydrazides with TBHP was efficiently developed, providing a variety of methyl sulfones with good to excellent yields. The reaction can be carried out in water smoothly without any ligand or additive under mild conditions and this catalyst-in-water can be recycled several times.

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