3-(3-cyano)propoxyl-acridine-9-carboxylic acid-(3-cyano)propyl ester | 126462-79-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 3-(3-cyano)propoxyl-acridine-9-carboxylic acid-(3-cyano)propyl ester
• 英文别名: 3-Cyanopropyl 3-(3-cyanopropoxy)acridine-9-carboxylate
• CAS: 126462-79-1
• 化学式: C₂₂H₁₉N₃O₃
• 分子量: 373.411
• InChiKey: BZTNXFGCLPCDPV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  96
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-(3-cyano)propoxyl-acridine-9-carboxylic acid-(3-cyano)propyl ester 以 甲醇 、 sodium hydroxide 为溶剂， 生成 3-(3-cyano)propoxyl-acridine-9-carboxylic acid
  参考文献：
  名称：

  Side-chain functional chemiluminescent labels and their conjugates, and

  摘要：

  一种化学发光化合物，具有一个含有芳基酯、硫酯或酰胺的杂环环或环系，该环或环系容易受到化学攻击而解离为瞬态化合物。该杂环环与酯、硫酯或酰胺基团的羰基相连，并具有一个杂原子处于氧化状态，使得通过解离与羰基相连的碳化合物发生化学发光。该杂环环或环系通过有机基团与其结合，并含有与活性氢含有化合物反应的官能团。芳环是一个环或环系，其环碳与酯、硫酯或酰胺的氧、硫或氮相连，并在六元环上含有取代基，起到空间和电子上的阻碍，以防止酯、硫酯或酰胺键的水解。可选地，在杂环环系的peri位上有一个电子给体取代基。芳环上的取代基至少包括一个ortho电子给体取代基，与peri取代基一起，至少包括两个邻接于酯、硫酯或酰胺键的电子给体取代基；芳环上至少有一个meta或para取代基，其.sigma..sub.p值大于0且小于1。还描述了使用这种标记化合物的检测和检测试剂盒。

  公开号：

  US05283334A1
• 作为产物：
  描述：

  3-hydroxy-acridine-9-carboxylic acid 、 4-溴丁腈 在 caesium carbonate 作用下， 以 氯仿 、 二甲基亚砜 为溶剂， 生成 3-(3-cyano)propoxyl-acridine-9-carboxylic acid-(3-cyano)propyl ester
  参考文献：
  名称：

  Side-chain functional chemiluminescent labels and their conjugates, and

  摘要：

  一种化学发光化合物，具有一个含有芳基酯、硫酯或酰胺的杂环环或环系，该环或环系容易受到化学攻击而解离为瞬态化合物。该杂环环与酯、硫酯或酰胺基团的羰基相连，并具有一个杂原子处于氧化状态，使得通过解离与羰基相连的碳化合物发生化学发光。该杂环环或环系通过有机基团与其结合，并含有与活性氢含有化合物反应的官能团。芳环是一个环或环系，其环碳与酯、硫酯或酰胺的氧、硫或氮相连，并在六元环上含有取代基，起到空间和电子上的阻碍，以防止酯、硫酯或酰胺键的水解。可选地，在杂环环系的peri位上有一个电子给体取代基。芳环上的取代基至少包括一个ortho电子给体取代基，与peri取代基一起，至少包括两个邻接于酯、硫酯或酰胺键的电子给体取代基；芳环上至少有一个meta或para取代基，其.sigma..sub.p值大于0且小于1。还描述了使用这种标记化合物的检测和检测试剂盒。

  公开号：

  US05283334A1

文献信息

• Assays utilizing improved chemiluminescent esters, thioesters and amides
  申请人：LONDON DIAGNOSTICS, INC.

  公开号：EP0322926A2

  公开（公告）日：1989-07-05

  In accordance with the present invention, specific binding assays are disclosed which utilize an chemiluminescent compound, i.e., moiety, which has increased stability in aqueous solution. The chemiluminescent moiety is an ester, thioester or amide in which the ester, thioester or amide linkage is between (1) a heterocyclic ring or ring system containing a carbon atom to which the linkage is attached, wherein the heteroatom within the heterocyclic ring or ring system is in an oxidation state which renders such carbon atom susceptible to attack by peroxide or molecular oxygen to form an intermediate which decays to produce chemiluminescence, and (2) an aryl ring or ring system. The aryl ring or ring system contains at least one substituted six-member ring. The substituted six-member ring has two or more substituent groups, where at least two of said two or more substituent groups sterically hinder hydrolysis of said linkage. One or more of the substituent groups which sterically hinder hydrolysis of said linkage may be an electron withdrawing group. The substituted six-member ring may have one or more additional substituent groups in addition to the substituent groups which sterically hinder hydrolysis of the linkage. Such additional substituent groups may also be an electron withdrawing group. The carbon atoms in the heterocyclic ring or ring system, to which the linkage is attached, may also have a secondary substituent of the formula RnX-, where X is selected from the group consisting of O, N, S and C, where R is any group, and where n is a number such that X has proper valency. Other chemiluminescent moieties are disclosed which are characterized by a heterocyclic ring or ring system and a secondary substituent of the formula RnX-, with the ester, thioester or amide linkage being between the heterocyclic ring or ring system and a leaving group. The disclosed chemiluminescent moieties can also include substituents at peri positions within the heterocyclic ring or ring system. Also in accordance with the present invention, compositions including and assay kits incorporating such chemiluminescent moieties are disclosed.

  根据本发明，公开了利用化学发光化合物（即在水溶液中稳定性更强的分子）进行特异性结合测定的方法。化学发光分子是酯类、硫酯类或酰胺类，其中酯类、硫酯类或酰胺类连接在 (1) 杂环或环系之间，杂环或环系含有一个碳原子，连接在该碳原子上，杂环或环系中的杂原子处于氧化状态，使该碳原子易受过氧化物或分子氧的侵蚀而形成中间体，中间体衰变产生化学发光；(2) 芳环或环系。芳基环或环系统包含至少一个取代的六元环。取代的六元环具有两个或两个以上的取代基，其中至少有两个取代基在立体上阻碍了所述连接的水解。其中一个或多个取代基团可以是取电子基团，这些取代基团立体地阻碍了所述连接的水解。取代的六元环除了具有立体阻碍水解连接的取代基团外，还可以具有一个或多个额外的取代基团。这些额外的取代基团也可以是取电子基团。 连接该连接体的杂环或环系中的碳原子也可以具有式 RnX- 的仲取代基，其中 X 选自 O、N、S 和 C 组成的组，R 为任意基团，n 为使 X 具有适当价数的数字。还公开了其他化学发光分子，其特征在于杂环或环系和式 RnX- 的仲取代基，酯、硫酯或酰胺连接在杂环或环系和离去基团之间。所公开的化学发光分子还可以包括杂环或环系周围位置的取代基。 根据本发明，还公开了包含此类化学发光分子的组合物和检测试剂盒。
• US5283334A
  申请人：——

  公开号：US5283334A

  公开（公告）日：1994-02-01
• US5284951A
  申请人：——

  公开号：US5284951A

  公开（公告）日：1994-02-08
• US5290936A
  申请人：——

  公开号：US5290936A

  公开（公告）日：1994-03-01
• Side-chain functional chemiluminescent labels and their conjugates, and
  申请人：London Diagnostics, Inc.

  公开号：US05283334A1

  公开（公告）日：1994-02-01

  A chemiluminescent compound possessing an aryl ester, thioester or amide of a carboxylic acid substituted heterocyclic ring or ring system that is susceptible to chemical attack to dissociate the heterocyclic ring to a transient compound. The heterocyclic ring is ring carbon-bonded to the carbonyl of the ester, thioester or amide moiety and possesses a heteroatom in an oxidation state that allows chemiluminescence by dissociating a compound at the carbon bonded to the carbonyl that decays to produce chemiluminescence. The heterocyclic ring or ring sustem contains bonded to it through an organic moiety, a functional group that is functionally reactive with an active hydrogen containing compound. The aryl ring is a ring or ring system that is ring carbon-bonded to the oxygen, sulfur or nitrogen of the ester, thioester or amide, as the case may be, and contains substituents on a six-member ring that act to sterically and electronically hinder hydrolysis of the ester, thioester or amide linkage. Optionally, there is an electron donating substituent in a peri position on the heterocyclic ring system. The substituents on the aryl ring comprise at least one ortho electron donating substitution that with the peri substitution comprises at least two substituents adjacent to the ester, thioester or amide linkage that are electron donors; at least one meta or para substituent on the aryl ring that possesses a .sigma..sub.p value greater than 0 and less than 1. Also described are assays and assay kits that employ such label compounds.

  一种化学发光化合物，具有一个含有芳基酯、硫酯或酰胺的杂环环或环系，该环或环系容易受到化学攻击而解离为瞬态化合物。该杂环环与酯、硫酯或酰胺基团的羰基相连，并具有一个杂原子处于氧化状态，使得通过解离与羰基相连的碳化合物发生化学发光。该杂环环或环系通过有机基团与其结合，并含有与活性氢含有化合物反应的官能团。芳环是一个环或环系，其环碳与酯、硫酯或酰胺的氧、硫或氮相连，并在六元环上含有取代基，起到空间和电子上的阻碍，以防止酯、硫酯或酰胺键的水解。可选地，在杂环环系的peri位上有一个电子给体取代基。芳环上的取代基至少包括一个ortho电子给体取代基，与peri取代基一起，至少包括两个邻接于酯、硫酯或酰胺键的电子给体取代基；芳环上至少有一个meta或para取代基，其.sigma..sub.p值大于0且小于1。还描述了使用这种标记化合物的检测和检测试剂盒。