2-[(4-Methylphenyl)imino]-1H-indene-1,3(2H)-dione | 60016-96-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-[(4-Methylphenyl)imino]-1H-indene-1,3(2H)-dione
• 英文别名: 2-(4-methylphenyl)iminoindene-1,3-dione
• CAS: 60016-96-8
• 化学式: C₁₆H₁₁NO₂
• 分子量: 249.269
• InChiKey: CFQLTTXBQBUCCF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  46.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[(4-Methylphenyl)imino]-1H-indene-1,3(2H)-dione 、 dimethyl (1S,12R,13S,14R,16S,17R)-3,10-dimethoxy-15-oxahexacyclo[10.5.1.02,11.04,9.013,17.014,16]octadeca-2,4,6,8,10-pentaene-14,16-dicarboxylate 以 二氯甲烷 为溶剂， 反应 2.0h， 以11%的产率得到spiro[dimethyl-3,10-dimethoxy-1α,12α,13β,14α,17α,18β-16,19-dioxahexacyclo[10,6,1.1^14,170^2,110^4,90^13,18]-dodeca-2,4,6,8,10-pentaene-14,17-dicarboxylate-15,1'-[2'-(p-tolylimino)-2'H-indene-3'-one]]
  参考文献：
  名称：

  Ninhydrin as a building block in scaffold-linked chromophoric dyad construction

  摘要：

  The reaction of ninhydrin with ester-activated cyclobutene epoxide (CE-1) containing the fused 1,4-dimethoxynaphthalene (DMN) chromophore, gave adducts formed by 1,3-dipolar cycloaddition at the central (C-2)-CO (major) and the outer (C-1,C-3)-CO (minor) positions. Conversion of the minor adduct to quinoxalines (QIN) by reaction with o-phenylenediamines at the alpha-dione moiety, albeit in poor yield, led to spiro-DMN-1,4 sigma-QIN dyad in which the plane of the chromophore was orthogonally orientated yet angled to the plane of the DMN chromophore. Reaction of ninhydrin with o-phenylenediamines yielded the corresponding 11-oxoindeno[1,2-b]quinoxalines which were coupled with CE-BLOCKs to form spiro adducts by reaction at the carbonyl site; the product from CE-1 was identical with that formed above. Another class of spiro-fused dyads was produced by reaction of ninhydrin with a primary amine followed by cycloaddition of CE-BLOCKs at the carbonyl site, where the amine was available to deliver one chromophore and the CE-BLOCK another.

  DOI：

  10.3998/ark.5550190.p008.520

文献信息

• Substrates for beta-lactamase and uses thereof
  申请人：Tsien Y. Roger

  公开号：US20070184513A1

  公开（公告）日：2007-08-09

  Substrates for β-lactamase of the general formula I in which one of X and Y is a fluorescent donor moiety and the other is a quencher (which may or may not re-emit); R′ is selected from the group consisting of H, lower (i.e., alkyl of 1 to about 5 carbon atoms) and (CH 2 ) n OH, in which n is 0 or an integer from 1 to 5; R″ is selected from the group consisting of H, physiologically acceptable metal and ammonium cations, CHR 2 OCO(CH 2 ) n CH 3 , —CHR 2 OCOC (CH 3 ) 3 , acylthiomethyl, acyloxy-alpha -benzyl, delta-butyrolactonyl, methoxycarbonyloxymethyl, phenyl, methylsulphinylmethyl, beta-morpholinoethyl, dialkylaminoethyl, acyloxyalkyl, dialkylaminocarbonyloxymethyl and aliphatic, in which R 2 is selected from the group consisting of H and lower alkyl; A is selected from the group consisting of S, O, SO, SO 2 and CH 2 ; and Z′ and Z″ are linkers for the fluorescent donor and quencher moieties. Methods of assaying β-lactamase activity and monitoring expression in systems using β-lactamase as a reporter gene also are disclosed.

  通式I的β-内酰胺酶底物，其中X和Y中的一个是荧光给体基团，另一个是猝灭剂（可以或不可以再发射）；R'从H，较低的（即1到约5个碳原子的烷基）和（CH2）nOH中选择，其中n为0或1到5的整数；R"从H，生理上可接受的金属和铵阳离子，CHR2OCO（CH2）nCH3，—CHR2OCOC（CH3）3，酰硫甲基，酰氧-α-苯甲基，δ-丁酰内酯，甲氧羰氧甲基，苯基，甲硫氧甲基，β-吗啡啉乙基，二烷基氨基乙基，酰氧烷基，二烷基氨基羰氧甲基和脂肪族中选择，其中R2从H和较低的烷基中选择；A从S，O，SO，SO2和CH2中选择；Z'和Z"是荧光给体和猝灭剂基团的连接器。还公开了评估β-内酰胺酶活性和使用β-内酰胺酶作为报告基因监测表达的方法。
• Novel fluorogenic substrates for beta-lactamase gene expression
  申请人：Tsien Y. Roger

  公开号：US20070020715A1

  公开（公告）日：2007-01-25

  Provided are fluorescent substrates β-lactamases and methods of using substrates having the general formulas: or in which where R 1 is H or A is S, O, SO, SO 2 or CH 2 ; X is O; L is a linker; R 2 is hydrogen; R 3 is hydrogen; R 4 is hydrogen; R 5 is hydrogen; R 6 is hydrogen; R 7 is hydrogen; R 8 is hydrogen; R 9 is in which W is a hydrogen, alkyl, substituted heteroalkyl, aryl, a heteroaryl, substituted heteroaryl or a CN; and, S is an integer from 0 to 5; W′ and W″ are independently hydrogen, alkyl, substituted heteroalkyl, aryl, substituted heteroaryl, (═O) or OR 10 ; wherein R 10 is hydrogen, substituted alkyl, heteroalkyl, substituted heteroalkyl, aryl, substituted aryl, heteroaryl; or substituted heteroaryl; and, Y is a dye moiety or a quencher moiety. R is a benzyl, 2-thienylmethyl, or cyanomethyl group; R′ is selected from the group consisting of H, physiologically acceptable salts or metal, ester groups, ammonium cations, —CHR 2 OCO(CH 2 ) n CH 3 , —CHR 2 OCOC(CH 3 ) 3 , acylthiomethyl, acyloxy-alpha-benzyl, deltabutyrolactonyl, methoxycarbonyloxymethyl, phenyl, methylsulphinylmethyl, β-morpholinoethyl, dialkylaminoethyl, and dialkylaminocarbonyloxymethyl, in which R 2 is selected from the group consisting of H and lower alkyl; A is selected from the group consisting of S, O, SO, SO 2 and CH 2 ; and Z is a donor fluorescent moiety. Also provided are methods of use of the compounds of the general formulas.
• US7157575B2
  申请人：——

  公开号：US7157575B2

  公开（公告）日：2007-01-02
• Ninhydrin as a building block in scaffold-linked chromophoric dyad construction
  作者：Davor Margetic、David A. Mann、Ronald N. Warrener

  DOI：10.3998/ark.5550190.p008.520

  日期：——

  The reaction of ninhydrin with ester-activated cyclobutene epoxide (CE-1) containing the fused 1,4-dimethoxynaphthalene (DMN) chromophore, gave adducts formed by 1,3-dipolar cycloaddition at the central (C-2)-CO (major) and the outer (C-1,C-3)-CO (minor) positions. Conversion of the minor adduct to quinoxalines (QIN) by reaction with o-phenylenediamines at the alpha-dione moiety, albeit in poor yield, led to spiro-DMN-1,4 sigma-QIN dyad in which the plane of the chromophore was orthogonally orientated yet angled to the plane of the DMN chromophore. Reaction of ninhydrin with o-phenylenediamines yielded the corresponding 11-oxoindeno[1,2-b]quinoxalines which were coupled with CE-BLOCKs to form spiro adducts by reaction at the carbonyl site; the product from CE-1 was identical with that formed above. Another class of spiro-fused dyads was produced by reaction of ninhydrin with a primary amine followed by cycloaddition of CE-BLOCKs at the carbonyl site, where the amine was available to deliver one chromophore and the CE-BLOCK another.