2,2,2-Trichloro-1-(4-nitro-1-{5-[4-nitro-2-(2,2,2-trichloro-acetyl)-pyrrol-1-yl]-pentyl}-1H-pyrrol-2-yl)-ethanone | 158628-10-5

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 2,2,2-Trichloro-1-(4-nitro-1-{5-[4-nitro-2-(2,2,2-trichloro-acetyl)-pyrrol-1-yl]-pentyl}-1H-pyrrol-2-yl)-ethanone
• 英文别名: 2,2,2-Trichloro-1-[4-nitro-1-[5-[4-nitro-2-(2,2,2-trichloroacetyl)pyrrol-1-yl]pentyl]pyrrol-2-yl]ethanone；2,2,2-trichloro-1-[4-nitro-1-[5-[4-nitro-2-(2,2,2-trichloroacetyl)pyrrol-1-yl]pentyl]pyrrol-2-yl]ethanone
• CAS: 158628-10-5
• 化学式: C₁₇H₁₄Cl₆N₄O₆
• 分子量: 583.039
• InChiKey: KDZAINZHCQHXTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  136
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,2,2-Trichloro-1-(4-nitro-1-{5-[4-nitro-2-(2,2,2-trichloro-acetyl)-pyrrol-1-yl]-pentyl}-1H-pyrrol-2-yl)-ethanone 在 platinum(IV) oxide 氢气 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 25.0~55.0 ℃ 、101.33 kPa 条件下， 反应 12.0h， 生成
  参考文献：
  名称：

  A New DNA Minor Groove Binding Motif: Cross-Linked Lexitropsins

  摘要：

  The nitrogen atoms of central pyrrole rings on two separate tripyrrolecarboxamide strands were covalently linked through poly(methylene) chains to provide a novel class of lexitropsins potentially capable of B-DNA double-strand reading via the minor groove, CD titration experiments revealed increasingly enhanced binding of 1:1 stoichiometry to the poly(dA-dT)-poly(dA-dT) DNA from the tetrakis(methylene) linkage to the heptakis(methylene) linkage, suggesting gradually growing importance of the bidentate antiparallel side by side binding. Ethidium bromide fluorescence displacement experiments on both poly(dA-dT)-poly(dA-dT) and poly(dA)-poly(dT) DNA's supported this analysis by providing quantitative measurement of intrinsic binding constants. The heptakis(methylene) linkage offered a binding enhancement of approximately 1000 times compared with that of the monomer.

  DOI：

  10.1021/ja00095a001
• 作为产物：
  描述：

  1,5-bis(N-pyrrolyl)pentane 在 硝酸 、 乙酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 27.58h， 生成 2,2,2-Trichloro-1-(4-nitro-1-{5-[4-nitro-2-(2,2,2-trichloro-acetyl)-pyrrol-1-yl]-pentyl}-1H-pyrrol-2-yl)-ethanone
  参考文献：
  名称：

  A New DNA Minor Groove Binding Motif: Cross-Linked Lexitropsins

  摘要：

  The nitrogen atoms of central pyrrole rings on two separate tripyrrolecarboxamide strands were covalently linked through poly(methylene) chains to provide a novel class of lexitropsins potentially capable of B-DNA double-strand reading via the minor groove, CD titration experiments revealed increasingly enhanced binding of 1:1 stoichiometry to the poly(dA-dT)-poly(dA-dT) DNA from the tetrakis(methylene) linkage to the heptakis(methylene) linkage, suggesting gradually growing importance of the bidentate antiparallel side by side binding. Ethidium bromide fluorescence displacement experiments on both poly(dA-dT)-poly(dA-dT) and poly(dA)-poly(dT) DNA's supported this analysis by providing quantitative measurement of intrinsic binding constants. The heptakis(methylene) linkage offered a binding enhancement of approximately 1000 times compared with that of the monomer.

  DOI：

  10.1021/ja00095a001

文献信息

• Design and synthesis of new thiazolated cross-linked DNA binding polyamides for altered sequence recognition
  作者：Sanjay K Sharma、Manju Tandon、J.William Lown

  DOI：10.1016/s0040-4020(02)00285-5

  日期：2002.4

  The design and synthesis are described for six new thiazolated versions of cross-linked polyamides (9a–f), in which the Th–Py–Py array of heterocycles is tethered from the central pyrrole by C5 and C7 methylene chains. The thiazole ring in the different cross-linked polyamides (9a–f) bears three different functional groups (viz. H, NHCHO and NH2). These six cross-linked polyamides were analyzed for

  描述和设计了六种新的噻唑基化版本的交联聚酰胺（9a - f），其中杂环的Th-Py-Py阵列通过C5和C7亚甲基链与中心吡咯相连。不同的交联聚酰胺（9a – f）中的噻唑环带有三个不同的官能团（即H，NHCHO和NH 2）。分析了这六种交联聚酰胺的促旋酶抑制特性，结果表明，由C7接头束缚的amTh–Py–Py（9b）对促旋酶的抑制浓度为（IC 50 = 0.01μM）是最有效的。到目前为止，在所有噻唑基化的交联聚酰胺中，该抑制剂均被分析。
• A New DNA Minor Groove Binding Motif: Cross-Linked Lexitropsins
  作者：Yong-Huang Chen、J. William Lown

  DOI：10.1021/ja00095a001

  日期：1994.8

  The nitrogen atoms of central pyrrole rings on two separate tripyrrolecarboxamide strands were covalently linked through poly(methylene) chains to provide a novel class of lexitropsins potentially capable of B-DNA double-strand reading via the minor groove, CD titration experiments revealed increasingly enhanced binding of 1:1 stoichiometry to the poly(dA-dT)-poly(dA-dT) DNA from the tetrakis(methylene) linkage to the heptakis(methylene) linkage, suggesting gradually growing importance of the bidentate antiparallel side by side binding. Ethidium bromide fluorescence displacement experiments on both poly(dA-dT)-poly(dA-dT) and poly(dA)-poly(dT) DNA's supported this analysis by providing quantitative measurement of intrinsic binding constants. The heptakis(methylene) linkage offered a binding enhancement of approximately 1000 times compared with that of the monomer.