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Revision as of 13:37, 9 August 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref') per Chem/Drugbox validation (report [[Wikipedia_talk:Wi← Previous edit		Latest revision as of 20:21, 28 August 2022 edit undoChinesePatrick (talk | contribs)8 edits →Surfactants
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	{{chembox		{{chembox
	| verifiedrevid = 443869801		| verifiedrevid = 443871329
	| ImageFile = Imidazoline numbering.png		| ImageFile = Imidazoline numbering.png
	| ImageSize =120px		| ImageSize =120px
			| ImageAlt = Skeletal formula of imidazoline
⚫	| IUPACName = 4,5-Dihydro-1''H''-imidazole
			| ImageFile1 = Imidazoline 3D ball.png
	| OtherNames =
			| ImageSize1 = 150
⚫	| Section1 = {{Chembox Identifiers
			| ImageAlt1 = Ball-and-stick model of the imidazoline molecule
		⚫	| PIN = 4,5-Dihydro-1''H''-imidazole
			| SystematicName = 1,3-Diazacyclopent-2-ene
			| OtherNames = 2-Imidazoline<br />4,5-Dihydro-1,3-diazole
		⚫	|Section1={{Chembox Identifiers
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 61464		| ChemSpiderID = 61464
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	| CASNo_Ref = {{cascite|correct|CAS}}		| CASNo_Ref = {{cascite|correct|CAS}}
	| CASNo = 504-75-6		| CASNo = 504-75-6
			| UNII_Ref = {{fdacite|correct|FDA}}
			| UNII = D36R5YLK6R
	| PubChem = 68156		| PubChem = 68156
	| ChEBI_Ref = {{ebicite|correct|EBI}}		| ChEBI_Ref = {{ebicite|correct|EBI}}
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	| SMILES = N\1=C\NCC/1		| SMILES = N\1=C\NCC/1
	}}		}}
	| Section2 = {{Chembox Properties		|Section2={{Chembox Properties
	| C=3|H=6|N=2		| C=3 | H=6 | N=2
	| Appearance =		| Appearance =
	| Density =		| Density =
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	| Solubility =		| Solubility =
	}}		}}
	| Section3 = {{Chembox Hazards		|Section3={{Chembox Hazards
	| MainHazards =		| MainHazards =
	| FlashPt =		| FlashPt =
	| Autoignition =		| AutoignitionPt =
	}}		}}
	}}		}}
	'''Imidazoline''' is a ]-containing ] with formula C<sub>3</sub>H<sub>6</sub>N<sub>2</sub>, derived from ]. The ring contains an ] bond, and the carbons at the 4 and 5 positions are singly bonded, rather than doubly bonded for the case of imidazole. Imidazolines are structurally related to ]s and ]s.		'''2-Imidazoline''' (]: '''4,5-dihydro-1''H''-imidazole''') is one of three isomers of the ]-containing ] ], with the formula C<sub>3</sub>H<sub>6</sub>N<sub>2</sub>. The 2-imidazolines are the most common imidazolines commercially, as the ring exists in some natural products and some pharmaceuticals. They also have been examined in the context of organic synthesis, coordination chemistry, and homogeneous catalysis.<ref name=Liu/>
			== Synthesis ==
	]<br style="clear:left;"/>
			]
			A variety of routes exist for the synthesis of imidazolines,<ref name=Liu/><ref>{{cite journal| vauthors = Crouch RD |title=Synthetic routes toward 2-substituted 2-imidazolines|journal=Tetrahedron|date=March 2009|volume=65|issue=12|pages=2387–2397|doi=10.1016/j.tet.2008.12.022}}</ref> with the most common methods involving the condensation of 1,2-diamines (e.g. ]) with ] or ]. The nitrile based route is essentially a cyclic ]; it requires high temperatures and acid catalysis and is effective for both alkyl and aryl nitriles.
			{{clear|left}}
			== As natural products ==
			Imidazoline has been found in various natural products. Natural molecules topsentin D and spongotine B were discovered in several marine sponges. These metabolites have received considerable attention because of their potent properties such as antitumor, antiviral, and anti-inflammatory activities.<ref>{{cite journal | vauthors = Guinchard X, Vallée Y, Denis JN | title = Total synthesis of marine sponge bis(indole) alkaloids of the topsentin class | journal = The Journal of Organic Chemistry | volume = 72 | issue = 10 | pages = 3972–3975 | date = May 2007 | pmid = 17444688 | doi = 10.1021/jo070286r }}</ref>
		⚫	== Biological role ==
⚫	]]]
		⚫	Many imidazolines are biologically active.<ref>{{cite journal | vauthors = Macinnes N, Duty S | title = Locomotor effects of imidazoline I2-site-specific ligands and monoamine oxidase inhibitors in rats with a unilateral 6-hydroxydopamine lesion of the nigrostriatal pathway | journal = British Journal of Pharmacology | volume = 143 | issue = 8 | pages = 952–959 | date = December 2004 | pmid = 15545290 | pmc = 1575965 | doi = 10.1038/sj.bjp.0706019 }}</ref> Most bio-active derivatives bear a substituent (] or ] group) on the carbon between the nitrogen centers. Some generic names include ], ], ], and ].
	Like imidazole, imidazoline-based compounds have been used as ] ligands on various transition metals. It is found in the commercially available second generation ].
			== Applications ==
⚫	==Biological role==
⚫	Many imidazolines are biologically active.<ref>{{cite journal | author = N. MacInnes and S. Duty | title = Locomotor effects of imidazoline I2-site-specific ligands and monoamine oxidase inhibitors in rats with a unilateral 6-hydroxydopamine lesion of the nigrostriatal pathway | year = 2004 | journal = ] | volume = 143 | issue = 8 | pages = 952–959 | doi = 10.1038/sj.bjp.0706019 | pmid = 15545290 | pmc = 1575965}}</ref> Most bio-active derivatives bear a substituent (] or ] group) on the carbon between the nitrogen centers. Some generic names include ], ], ], and ].
	==See also==		=== Pharmaceutical ===
			2-imidazolines have been investigated as antihyperglycemic, anti-inflammatory, antihypertensive, antihypercholesterolemic, and antidepressant reagents.<ref name=Liu>{{cite journal | vauthors = Liu H, Du DM | date = March 2009 | title = Recent Advances in the Synthesis of 2-Imidazolines and Their Applications in Homogeneous Catalysis | journal = Advanced Synthesis & Catalysis | volume = 351 | issue = 4 | pages = 489–519 | doi = 10.1002/adsc.200800797 }}</ref><ref>{{cite journal | vauthors = Dardonville C, Rozas I | title = Imidazoline binding sites and their ligands: an overview of the different chemical structures | journal = Medicinal Research Reviews | volume = 24 | issue = 5 | pages = 639–661 | date = September 2004 | pmid = 15224384 | doi = 10.1002/med.20007 | s2cid = 31258438 }}</ref> The imidazoline-containing drug clonidine is used alone or in combination with other medications to treat high blood pressure. It is also used in the treatment of dysmenorrhea, hypertensive crisis, Tourette's syndrome and attention deficit hyperactivity disorder (ADHD).<ref>{{cite web | title = Clonidine | date = October 2008 | work = Pubmed Health | url = https://www.ncbi.nlm.nih.gov/pubmedhealth/PMH0000623/ | archive-url = https://web.archive.org/web/20100628173619/https://www.ncbi.nlm.nih.gov/pubmedhealth/PMH0000623/ | archive-date = 28 June 2010 }}</ref>
			<gallery caption="2-Imidazolines" widths="180px" heights="120px" perrow="4">
			File:Clonidine.png|Clonidine
			File:Example_of_imidazoline_as_catalyst.png|Biimidazoline ligands and a complex.
		⚫	File:Grubbs_catalyst_Gen2.svg|Second generation ]
			File:Spongotine B.png|Spongotine B
			</gallery>
			==== As p53 activators ====
			''Cis''-imidazolines act as small-molecule antagonists of ]. These compounds bind MDM2/X in the p53-binding pocket and activate the p53 pathway in cancer cells, leading to cell cycle arrest, apoptosis, and growth inhibition of human tumor xenografts in nude mice. The most active compounds are ]<ref>{{cite journal | vauthors = Vassilev LT, Vu BT, Graves B, Carvajal D, Podlaski F, Filipovic Z, Kong N, Kammlott U, Lukacs C, Klein C, Fotouhi N, Liu EA | display-authors = 6 | title = In vivo activation of the p53 pathway by small-molecule antagonists of MDM2 | journal = Science | volume = 303 | issue = 5659 | pages = 844–848 | date = February 2004 | pmid = 14704432 | doi = 10.1126/science.1092472 | bibcode = 2004Sci...303..844V | s2cid = 16132757 }}</ref> and rg-7112,<ref>{{cite journal | vauthors = Vu B, Wovkulich P, Pizzolato G, Lovey A, Ding Q, Jiang N, Liu JJ, Zhao C, Glenn K, Wen Y, Tovar C, Packman K, Vassilev L, Graves B | display-authors = 6 | title = Discovery of RG7112: A Small-Molecule MDM2 Inhibitor in Clinical Development | journal = ACS Medicinal Chemistry Letters | volume = 4 | issue = 5 | pages = 466–469 | date = May 2013 | pmid = 24900694 | pmc = 4027145 | doi = 10.1021/ml4000657 }}</ref> but some other analogs also activate p53.<ref>{{Cite journal | vauthors = Bazanov DR, Pervushin NV, Savin EV, Tsymliakov MD, Maksutova AI, Sosonyuk SE, Kopeina GS, Lozinskaya NA | display-authors = 6 |date=December 2021 |title=Sulfonamide derivatives of cis-imidazolines as potent p53-MDM2/MDMX protein-protein interaction inhibitors |url=https://link.springer.com/10.1007/s00044-021-02802-w |journal=Medicinal Chemistry Research |language=en |volume=30 |issue=12 |pages=2216–2227 |doi=10.1007/s00044-021-02802-w | s2cid = 241788123 |issn=1054-2523}}</ref><ref>{{cite journal | vauthors = Bazanov DR, Pervushin NV, Savitskaya VY, Anikina LV, Proskurnina MV, Lozinskaya NA, Kopeina GS | title = 2,4,5-Tris(alkoxyaryl)imidazoline derivatives as potent scaffold for novel p53-MDM2 interaction inhibitors: Design, synthesis, and biological evaluation | journal = Bioorganic & Medicinal Chemistry Letters | volume = 29 | issue = 16 | pages = 2364–2368 | date = August 2019 | pmid = 31196710 | doi = 10.1016/j.bmcl.2019.06.007 | s2cid = 189815065 }}</ref><ref>{{cite journal | vauthors = Bazanov DR, Pervushin NV, Savin EV, Tsymliakov MD, Maksutova AI, Savitskaya VY, Sosonyuk SE, Gracheva YA, Seliverstov MY, Lozinskaya NA, Kopeina GS | display-authors = 6 | title = Synthetic Design and Biological Evaluation of New p53-MDM2 Interaction Inhibitors Based on Imidazoline Core | journal = Pharmaceuticals | volume = 15 | issue = 4 | pages = 444 | date = April 2022 | pmid = 35455441 | pmc = 9027661 | doi = 10.3390/ph15040444 | doi-access = free }}</ref>
			=== Surfactants ===
			]s based around 2-imidazoline, such as ], are used in personal care products where mildness and non-irritancy are particularly important (e.g. baby products, "no more tears" shampoos etc.).<ref>{{cite journal | vauthors = Tyagi R, Tyagi VK, Pandey SK | title = Imidazoline and its derivatives: an overview | journal = Journal of Oleo Science | volume = 56 | issue = 5 | pages = 211–222 | year = 2007 | pmid = 17898484 | doi = 10.5650/jos.56.211 | doi-access = free }}</ref>
			=== As precursors of imidazoles ===
			Imidazoles can be prepared from dehydrogenation of imidazolines.<ref>{{cite journal | vauthors = Ishihara M, Togo H | year = 2006 | title = An Efficient Preparation of 2-Imidazolines and Imidazoles from Aldehydes with Molecular Iodine and (Diacetoxyiodo)benzene | journal = Synlett | issue = 2 | pages = 227–230 | doi = 10.1055/s-2005-923604 }}</ref>
			=== Homogeneous catalysis ===
			As a structural analogue of 2-oxazolines, 2-imidazolines have been developed as ligands in coordination chemistry. The substitutions on the nitrogen atom in the imidazoline ring provide opportunities for fine-tuning the electronic and steric properties. Some of the complexes function as catalysts for Suzuki–Miyaura couplings, Mizoroki–Heck reactions, Diels–Alder reactions, asymmetric allylic substitution, sigmatropic rearrangement, Henry reactions, etc.<ref name=Liu/>
			]
			== See also ==
	* ]		* ]
	* ]		* ]
	==References==		== References ==
	{{reflist}}		{{reflist}}
			{{DEFAULTSORT:Imidazoline, 2-}}
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