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[ CAS No. 4097-89-6 ] {[proInfo.proName]}

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Chemical Structure| 4097-89-6
Chemical Structure| 4097-89-6
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Product Citations

Product Citations

Xuexiang Han ; Mohamad-Gabriel Alameh ; Ningqiang Gong , et al. DOI: PubMed ID:

Abstract: Lipid nanoparticles (LNPs) are widely used for mRNA delivery, with cationic lipids greatly afecting biodistribution, cellular uptake, endosomal escape and transfection efciency. However, the laborious synthesis of cationic lipids limits the discovery of efcacious candidates and slows down scale-up manufacturing. Here we develop a one-pot, tandem multi-component reaction based on the rationally designed amine-thiol-acrylate conjugation, which enables fast (1?h) and facile room-temperature synthesis of amidine-incorporated degradable (AID) lipids. Structure-activity relationship analysis of a combinatorial library of 100 chemically diverse AID-lipids leads to the identifcation of a tail-like amine-ring-alkyl aniline that generally afords efcacious lipids. Experimental and theoretical studies show that the embedded bulky benzene ring can enhance endosomal escape and mRNA delivery by enabling the lipid to adopt a more conical shape. The lead AID-lipid can not only mediate local delivery of mRNA vaccines and systemic delivery of mRNA therapeutics, but can also alter the tropism of liver-tropic LNPs to selectively deliver gene editors to the lung and mRNA vaccines to the spleen.

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Product Details of [ 4097-89-6 ]

CAS No. :4097-89-6 MDL No. :MFCD00008177
Formula : C6H18N4 Boiling Point : -
Linear Structure Formula :N((CH2)2NH2)3 InChI Key :MBYLVOKEDDQJDY-UHFFFAOYSA-N
M.W : 146.23 Pubchem ID :77731
Synonyms :
Chemical Name :N1,N1-Bis(2-aminoethyl)ethane-1,2-diamine

Safety of [ 4097-89-6 ]

Signal Word:Danger Class:8,6.1
Precautionary Statements:P280-P301+P310-P302+P350-P305+P351+P338-P310 UN#:2922
Hazard Statements:H301-H310-H314 Packing Group:Ⅱ
GHS Pictogram:

Application In Synthesis of [ 4097-89-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 4097-89-6 ]

[ 4097-89-6 ] Synthesis Path-Downstream   1~14

  • 1
  • [ 4097-89-6 ]
  • [ 99970-84-0 ]
  • [ 131385-20-1 ]
  • 2
  • [ 4097-89-6 ]
  • [ 99970-84-0 ]
  • [ 131385-20-1 ]
  • 3
  • [ 55589-47-4 ]
  • [ 4097-89-6 ]
  • N-[1-(3-Methyl-pyridin-2-yl)-meth-(E)-ylidene]-N',N'-bis-(2-[1-(3-methyl-pyridin-2-yl)-meth-(E)-ylidene]-amino}-ethyl)-ethane-1,2-diamine [ No CAS ]
  • 4
  • dysprosium(III) nitrate hydrate [ No CAS ]
  • [ 4097-89-6 ]
  • [ 32596-43-3 ]
  • copper(II) perchlorate [ No CAS ]
  • [ 75-05-8 ]
  • [DyCu(N(CH2CH2NCHC6H2(O)(Cl)CHNCH2CH2)3N)(CH3)2NCHO](2+)*2ClO4(1-)*CH3CN=[CuDy(C39H43Cl3N9O4)](ClO4)2*CH3CN [ No CAS ]
  • 5
  • terbium(III) nitrate hexahydrate [ No CAS ]
  • [ 4097-89-6 ]
  • [ 32596-43-3 ]
  • Tb(3+)*N((CH2CH2NCH)2C6H2(OH)(Cl))2((CH2CH2NCH)2C6H2(O)(Cl))N(1-)*2NO3(1-)*10H2O=[C36H40N9O7Cl3Tb](NO3)*9H2O [ No CAS ]
  • 6
  • europium(III) nitrate hexahydrate [ No CAS ]
  • [ 4097-89-6 ]
  • [ 32596-43-3 ]
  • Eu(3+)*N((CH2CH2NCH)2C6H2(OH)(Cl))3N*3NO3(1-)*H2O=[Eu(N((CH2CH2NCH)2C6H2(OH)(Cl))3N)(NO3)(H2O)](NO3)2 [ No CAS ]
  • 7
  • europium(III) nitrate hexahydrate [ No CAS ]
  • [ 4097-89-6 ]
  • [ 32596-43-3 ]
  • Eu(3+)*N((CH2CH2NCH)2C6H2(OH)(Cl))2((CH2CH2NCH)2C6H2(O)(Cl))N(1-)*2NO3(1-)*5H2O=[C36H40N9O7Cl3Eu](NO3)*4H2O [ No CAS ]
  • 8
  • [ 4097-89-6 ]
  • LaCl3*8H2O [ No CAS ]
  • [ 32596-43-3 ]
  • La(3+)*(CHOC6H2OHClCHNCH2CH2)3N(3-) = La[(CHOC6H2OHClCHNCH2CH2)3N] [ No CAS ]
  • 9
  • [ 4097-89-6 ]
  • LaCl3*8H2O [ No CAS ]
  • [ 32596-43-3 ]
  • La(3+)*(CH(OCH3)2OHC6H2ClCHNCH2CH2)3N(3-)*5H2O = La[(CH(OCH3)2OHC6H2ClCHNCH2CH2)3N]*5H2O [ No CAS ]
  • 10
  • [ 4097-89-6 ]
  • [ 28170-07-2 ]
  • [ 247170-99-6 ]
YieldReaction ConditionsOperation in experiment
75% In ethanol; at 0 - 20℃; This is also a known compound, (Jap. Pat. No. 11302243, Takayanagi, Hisao, Mitsubishi Chemical Industries). The patent reported a multi-step synthesis using ethylenediamine as a starting material. We found that compound E-IO can be prepared in a one step reaction under mild conditions:[0212] Benzyl Phenyl Carbonate* (Pittelkow, et al, Synthesis, 2002, 2195) (4.56 g, 20 mmol) was added to a stirring solution of TREN (1.46 g, 10 mmol) in absolute EtOH (50 mL) while cooling with an ice bath. The reaction mixture was stirred over night at room temperature. The volatiles were removed in vacuo, dissolved in minimum amount Of CH2Cl2 and loaded onto a flash silica column; compound E-IO was separated by gradient chromatography with 3-10 % CH3OH + 1% TEA in CH2Cl2. The isolated appropriate fractions were combined and pass through a strong basic alumina plug, and concentrated to afford pure BisZ-TREN as a thick colorless oil at 75 % yield.[0213] 1H NMR (500 MHz, CDCl3, 25 0C): delta 2.48 (t, 2H, J = 5.5Hz, CH2), 2.56 (s,br, 4H, CH2), 2.67 (t, 2H, J = 5.5Hz, CH2), 3.23 (s,br, 4H, CH2), 5.06 (s, 2H, CH2), 5.72 (s, 2H, CbzNH), 7.04 (m, 1OH, ArH). 13C NMR (500 MHz, CDCl3): delta, 38.91,39.35, 53.82, 52.69, 66.28, 127.78, 127.82, 136.58, 156.70. MS (FAB, NBA) C22H30N4O4: [M+H]+ 415.
Example 1: Synthesis of the Macrocyclic Ligand (4); [0243] A variety of synthetic routes were pursued to obtain derivatized versions of compound 3. Those efforts lead to a method for the synthesis of compound 4. The derivatized building block used in the synthesis of 4 is prepared from lysine and tris(2-aminoethyl)amine (TREN) as outlined in Scheme 1 below.Scheme 1hydrogenation 18 19[0244] Reductive amination of the protected lysine derivative 22 using Z-protected tris(2- aminoethyl)amine (TREN) led to the intermediate 17, which was further derivatized by reaction with a protected aziridine. Removal of the Z-protection groups by hydrogenation afforded the carbonate salt 18, which was transformed into the corresponding free base. The <n="74"/>Boc-protected molecule 19 was then used to prepare compound 4 as outlined in Scheme 2 below.
  • 11
  • [ 4097-89-6 ]
  • [ 10165-86-3 ]
  • [ 1409937-00-3 ]
  • 12
  • [ 7089-68-1 ]
  • [ 4097-89-6 ]
  • C30H30N8*4ClH [ No CAS ]
  • C42H36N10*4ClH [ No CAS ]
  • 13
  • [ 55750-49-7 ]
  • [ 4097-89-6 ]
  • [ 139112-38-2 ]
  • 14
  • [ 4097-89-6 ]
  • [ 74205-82-6 ]
  • N',N'?bis((1H?1,2,4?triazol?1?yl)methyl)?N'',N''?bis(2?(bis((1H?1,2,4?triazol?1?yl)methyl)amino)ethyl)ethane?1,2?diamine [ No CAS ]
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