(9ci)-1H-呋喃并[3,4-f]苯并咪唑-5,7-二酮 | 167993-16-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 中文名称: (9ci)-1H-呋喃并[3,4-f]苯并咪唑-5,7-二酮
• 英文名称: benzimidazole-5,6-dicarboxylic acid anhydride
• 英文别名: 1H-Furo[3,4-f]benzimidazole-5,7-dione；3H-furo[3,4-f]benzimidazole-5,7-dione
• CAS: 167993-16-0
• 化学式: C₉H₄N₂O₃
• 分子量: 188.142
• InChiKey: LSJKEARWMQPUEK-UHFFFAOYSA-N

物化性质

• 沸点：
  574.7±23.0 °C(Predicted)
• 密度：
  1.738±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  72
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (9ci)-1H-呋喃并[3,4-f]苯并咪唑-5,7-二酮 在 N,N-二异丙基乙胺 、 bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 27.5h， 生成 dibenzyl 5-[[(2S)-2-[[6-(1-adamantylmethylcarbamoyl)-1H-benzimidazole-5-carbonyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]benzene-1,3-dicarboxylate
  参考文献：
  名称：

  基于双环，杂芳香族骨架的非肽胆囊收缩素-B /胃泌素受体拮抗剂。

  摘要：

  最近在大鼠和狗模型中发现，发现了一系列基于二苯并双环[2.2.2]辛烷（BCO）骨架的强效和选择性胆囊收缩素B /胃泌素受体拮抗剂，它们显示出物种依赖性的行为。我们现在报告发现其中BCO骨架已被双环，杂芳族骨架（例如5，6-二取代的吲哚或苯并咪唑）取代的化合物的发现。这些新的配体在体外保持了先前化合物的亲和力和选择性，但在体内却表现出更加一致的行为模式。当以0.1μmol·kg-1或更少的剂量静脉内施用时，已经表明这类化合物的代表性实例抑制五肽胃泌素刺激的酸分泌。

  DOI：

  10.1021/jm9508907
• 作为产物：
  描述：

  indole-5,6-dicarboxylic acid anhydride 生成 (9ci)-1H-呋喃并[3,4-f]苯并咪唑-5,7-二酮
  参考文献：
  名称：

  Gastin and CCK receptor ligands

  摘要：

  式(Ia)、(Ib)或(Ic)的化合物，其中A代表具有两个融合环的基团，或者代表式(Id)的基团，R.sup.1.sub.(m)代表多达6个取代基，K代表--O--、--S--、--CH.sub.2--、--N(R.sup.2)--或--N(COR.sup.2)--，其中R.sup.2为H或C.sub.1到C.sub.3烷基，W为羰基、磺酰基或亚砜基，前提是W和X中至少有一个含有羰基，Y和Z如描述中所示，它们的药学上可接受的盐是CCK和/或胃泌素受体的配体。

  公开号：

  US05795907A1

文献信息

• CCK2 receptor antagonists containing the conformationally constrained phenylalanine derivatives, including the new amino acid Xic
  作者：Susan E Gibson (née Thomas)、Nathalie Guillo、Jerome O Jones、Ildiko M Buck、S.Barret Kalindjian、Sonia Roberts、Matthew J Tozer

  DOI：10.1016/s0223-5234(02)01351-x

  日期：2002.5

  The conformationally constrained analogues of phenylalanine, tetrahydroisoquinoline-3-carboxylic acid (Tic), Sic, Hic and Nic, and the new amino acid Xic have been incorporated into a potent and highly selective cholecystokinin-2 (CCK(2)) receptor antagonist (2) in place of the phenylalanine residue, producing compounds 15a-e. High selectivities for CCK(2) over CCK(1) were observed for compounds 15a-e

  苯丙氨酸，四氢异喹啉-3-羧酸（Tic），Sic，Hic和Nic以及新氨基酸Xic的构象约束类似物已被纳入有效且高度选择性的胆囊收缩素2（CCK（2））受体拮抗剂（ 2）代替苯丙氨酸残基，产生化合物15a-e。对于化合物15a-e，与CCK（1）相比，CCK（2）的选择性高。含有Nic残基（15d）的类似物的体外概况与化合物2相同，而其他构象限制条件则导致亲和力显着下降。Nic在这些CCK（2）配体的上下文中的明显优势随后被证明具有统计学意义。
• Gastrin and CCK antagonists
  申请人：James Black Foundation Limited

  公开号：US05912260A1

  公开（公告）日：1999-06-15

  Described herein are compounds of formula (I) or a pharmaceutically acceptable salt thereof, ##STR1## wherein L is N or C, one of X and Y is --NH--CH.sub.2 --R.sup.2 and the other is the substituent of formula (II). The compounds are potent gastrin and/or CCK antagonists.

  本文描述了式（I）的化合物或其药学上可接受的盐，其中L为N或C，X和Y中的一个是--NH--CH.sub.2--R.sup.2，另一个是式（II）的取代基。这些化合物是强效的胃泌素和/或CCK拮抗剂。
• Gastrin and cck receptor ligands
  申请人：James Black Foundation Limited

  公开号：US05919829A1

  公开（公告）日：1999-07-06

  Compounds of formula (Ia), (Ib), or (Ic), wherein A represents a group having two fused rings, or a group of formula (Id), R.sup.1.sub.(m) represents up to 6 substituents, K represents --O--, --S--, --CH.sub.2 --, --N(R.sup.2)-- or --N(COR.sup.2)--, in which R.sup.2 is H or C.sub.1 to C.sub.3 alkyl, W is a carbonyl, sulfonyl or sulfinyl group, provided that at least one of W and X contains carbonyl, Y and Z are as given in the description, and their pharmaceutically acceptable salts are ligands at CCK and/or gastrin receptors. ##STR1##

  化合物的式子(Ia)，(Ib)或(Ic)，其中A代表具有两个融合环的基团，或式子(Id)的基团，R.sup.1.sub.(m)代表最多6个取代基，K代表--O--，--S--，--CH.sub.2--，--N(R.sup.2)--或--N(COR.sup.2)--，其中R.sup.2是H或C.sub.1到C.sub.3烷基，W是一个羰基，磺酰基或亚磺酰基基团，但至少其中的一个W和X含有羰基，Y和Z如所述，在CCK和/或胃泌素受体上具有药理学上可接受的盐。##STR1##
• Size-Expanded Analogues of dG and dC:  Synthesis and Pairing Properties in DNA
  作者：Haibo Liu、Jianmin Gao、Eric T. Kool

  DOI：10.1021/jo048357z

  日期：2005.1.1

  We describe the completion of the set of four benzo-fused expanded DNA (xDNA) nucleoside analogues. We previously reported the development of benzo-fused analogues of dA and dT and their inclusion in an exceptionally stable new four-base genetic system. termed xDNA. in which the base pairs were expanded in size. Here we describe the preparation and properties of the-second half of this nucleotide set: namely, the previously unknown dxC and dxG nucleosides. The dxC analogue was prepared from the previously reported dxT nucleoside in three steps and 57%, yield. The large-sized deoxyguanosine analogue was prepared from an intermediate in the synthesis of dxA, yielding dxG in 14 steps overall (2.4%). Suitably protected versions of the deoxynucleosides were prepared for oligonucleotide synthesis following standard procedures, and they were readily incorporated into DNA by automated synthesizer. "Dangling-end" measurements revealed that the benzo-fused homologues stack considerably more strongly on neighbor DNA sequences h do their natural counterparts. Base pairing experiments with xC or xG bases showed that they pair selectively with their Watson-Crick partners, but with mild destabilization. due apparently to their larger size. Overall, the data suggest that the fluorescent xG and xG bases may he useful probes of steric effects in the study of biological nucleotide recognition mechanisms. In addition. the completion of the xDNA nucleoside set makes it possible in the future to construct full four-base xDNA strands that can target any sequence of natural DNA and RNA.
• INCORPORATION OF CONFORMATIONALLY CONSTRAINED PHENYLALANINE DERIVATIVES TIC, SIC, HIC AND NIC INTO A CHOLECYSTOKININ-B/GASTRIN RECEPTOR ANTAGONIST
  作者：Susan E Gibson、Nathalie Guillo、S.Barret Kalindjian、Matthew J Jozer

  DOI：10.1016/s0960-894x(97)00211-4

  日期：1997.5

  The preparation and biological properties of a conformationally constrained series of cholecystokinin-B/gastrin receptor ligands are described. The 9-membered ring (Nic) derivative was found to be as active at these receptors as an unconstrained phenylalanine analogue. (C) 1997 Elsevier Science Ltd.