289-80-5 Usage
Chemical Description
Pyridazine is a heterocyclic compound containing a six-membered ring with two nitrogen atoms.
Description
Pyridazine, sometimes called 1,2-diazine, is a six-membered ring containing two adjacent nitrogen atoms. Pyridazine is a privileged structure in medicinal chemistry and can be used as an isosteric replacement of phenyl or heteroaromatic rings. Pyridazines can improve the physiochemical properties of drug molecules by increasing their water solubility, participating as hydrogen bond acceptors, and have a high capacity to complex with targets due to their dipole moment. Pyridazine confers bioavailability, especially to the CNS, and can reduce toxicity. Pyridazine is a part of several drug molecules, and the pyradzine pharmacophore has led to a variety of pharmacologically active compounds.
Heterocyclic compound
Pyridazine refers to a heterocyclic azine compound containing a nitrogen hexaheterocyclic , it and pyrimidine, pyrazine are isomers of each other , it is insoluble in petroleum ether, soluble in methanol, ethanol and ether, and it can be miscible with water, benzene and dimethyl formamide immiscibility. Pyridazine is a weak base, which can form salts with picric acid, and hydrochloric acid; pyridazine is not prone to nucleophilic and electrophilic aromatic substitution reaction; it is stable to potassium permanganate; sodium or alcohols may be reduced open-chain , and converted to 1,4-diaminobutane. Pyridazine is widely used as pharmaceutical raw materials, such as long-term sulfa SMP which is pyridazine derivative, 4-amino-cinnoline which belongs to antimalarials, blood pressure drug hydralazine, etc. all use pyridazine as raw materials; it can also be used as raw material of pesticides, for the production of herbicides, "herbicide-sensitive", "Milstem", "bromine herbicide-sensitive", "Kusakira," "maleic hydrazide", "Norflurazon", "pyridate "" insecticide "," imputed phosphorus "and so on.
Synthesis and Structure
Pyridazines are heterocyclic compounds with an N-N bond in their ring structure. The pyridazine molecule is a π-deficient heteroaromatic compound similar to pyridine. Due to the presence of the π-deficient nitrogen aromatic heterocycles these compounds are more easily soluble in water when compared to other hydrocarbons. The basic aromatic ring system of pyridazine contains two adjacent nitrogen atoms.
The parent heterocycle was first prepared by oxidation of benzocinnoline to the pyridazinetetracarboxylic acid followed by decarboxylation. A better route to this otherwise esoteric compound starts with the maleic hydrazide. These heterocycles are often prepared via condensation of 1,4-diketones or 4-ketoacids with hydrazines.
Pyridazines are effective water oxidation catalysts with high efficiency turnover numbers up to 700.
Chemical Properties
Clear yellowish-brown liquid
Uses
Pyrrolo[1,2-b]pyridazine 1 is a N-bridgehead aromatic heterocycle containing two nitrogen atoms, is obtained by the condensation of pyridazine and pyrrole.
General Description
Pyridazine is a mono-basic 1,2-diazine compound, which is commonly prepared by the reaction of 1,4-dicarbonyls with hydrazines. Pyridazine ring is found in many herbicides like credazine, pyridatol and many pharmaceutical drugs like cefozopran, olaparib, talazoparib, and cadralazine.
Safety Profile
Moderately toxic by intraperitoneal route. When heated to decomposition it emits toxic vapors of NOx.
Check Digit Verification of cas no
The CAS Registry Mumber 289-80-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 2,8 and 9 respectively; the second part has 2 digits, 8 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 289-80:
(5*2)+(4*8)+(3*9)+(2*8)+(1*0)=85
85 % 10 = 5
So 289-80-5 is a valid CAS Registry Number.
InChI:InChI=1/C4H4N2/c1-2-4-6-5-3-1/h1-4H
289-80-5Relevant articles and documents
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Stanovnik et al.
, p. 3059 (1978)
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Approaches to open fullerenes: Synthesis and kinetic stability of Diels-Alder adducts of substituted isobenzofurans and C60
Chuang, Shih-Ching,Sander, Michael,Jarrosson, Thibaut,James, Scott,Rozumov, Eugene,Khan, Saeed I.,Rubin, Yves
, p. 2716 - 2723 (2007)
(Chemical Equation Presented) We have examined the reactions of 1,3-disubstituted isobenzofurans with the fullerene C60 in the context of an approach to open a large orifice on the fullerene framework. A variety of substituted isobenzofurans (6a-h), generated from the reaction of 1,4-substituted 1,4-epoxynaphthalenes 3a-h with 3,6-bis(2-pyridyl)-1,2,4,5- tetrazine (4a) or 1,2,4,5-tetrazine (4b), were added to C60 to afford the Diels-Alder adducts 7a-h. The thermal stability of these adducts toward retro-Diels-Alder fragmentation differs greatly in solution from that in the solid state. In solution, the relatively facile retro-Diels-Alder fragmentation of monoadducts 7a and 7c, to give C60 and the free isobenzofurans 6a and 6c, have rate constants (and activation barriers) of k = 9.29 × 10-5 s-1 at 70°C (Ea = 32.6 kcal mol -1) and k = 1.36 × 10-4 s-1 at 40°C (Ea = 33.7 kcal mol-1), respectively, indicating that the addition of isobenzofurans to C60 is readily reversible at those temperatures. In the solid state, thermogravimetric analysis of adduct 7a indicates that its decomposition occurs only within the temperature range of 220-300°C. As a result, these compounds can be stored at room temperature in the solid state for several weeks without significant decomposition but have to be handled within several hours in solution.
Synthesis of novel 7-azaindole derivatives containing pyridin-3-ylmethyl dithiocarbamate moiety as potent PKM2 activators and PKM2 nucleus translocation inhibitors
Liu, Bin,Yuan, Xia,Xu, Bo,Zhang, Han,Li, Ridong,Wang, Xin,Ge, Zemei,Li, Runtao
, p. 1 - 15 (2019/03/17)
Multiple lines of evidence have indicated that pyruvate kinase M2 (PKM2) is upregulated in most cancer cells and it is increasingly recognized as a potential therapeutic target in oncology. In a continuation of our discovery of lead compound 5 and SAR study, the 7-azaindole moiety in compound 5 was systematically optimized. The results showed that compound 6f, which has a difluoroethyl substitution on the 7-azaindole ring, exhibited high PKM2 activation potency and anti-proliferation activities on A375 cell lines. In a xenograft mouse model, oral administration of compound 6f led to significant tumor regression without obvious toxicity. Further mechanistic studies revealed that 6f could influence the translocation of PKM2 into nucleus, as well as induction of apoptosis and autophagy of A375 cells. More importantly, compound 6f significantly inhibited migration of A375 cells in a concentration-dependent manner. Collectively, 6f may serve as a lead compound in the development of potent PKM2 activators for cancer therapy.
METHODS OF INCORPORATING AN AMINO ACID COMPRISING A BCN GROUP INTO A POLYPEPTIDE USING AN ORTHOGONAL CODON ENCODING IT AND AN ORTHORGONAL PYLRS SYNTHASE
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Page/Page column, (2015/06/03)
The invention relates to a polypeptide comprising an amino acid having a bicyclo[6.1.0]non-4-yn-9-ylmethanol (BCN) group, particularly when said BCN group is present as: a residue of a lysine amino acid. The invention also relates to a method of producing a polypeptide comprising a BCN group, said method comprising genetically incorporating an amino acid comprising a BCN group into a polypeptide. The invention also relates to an amino acid comprising bicyclo[6.1.0]non-4-yn-9-ylmethanol (BCN), particularly and amino acid which is bicyclo[6.1.0]non-4-yn-9-ylmethanol (BCN) lysine. In addition the invention relates to a PylRS tRNA synthetase comprising the mutations Y271M, L274G and C313A.
