2-{[(1H)-pyrrole-2-carbonyl]amino}benzoic acid | 89812-79-3

• 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-{[(1H)-pyrrole-2-carbonyl]amino}benzoic acid
• 英文别名: N-(2-Carboxyphenyl)-pyrrole-2-carboxamide；Benzoic acid, 2-[(1H-pyrrol-2-ylcarbonyl)amino]-；2-(1H-pyrrole-2-carbonylamino)benzoic acid
• CAS: 89812-79-3
• 化学式: C₁₂H₁₀N₂O₃
• mdl: MFCD11167886
• 分子量: 230.223
• InChiKey: XYYCFMRMTICCHI-UHFFFAOYSA-N

物化性质

• 熔点：
  276-277 °C (decomp)
• 沸点：
  377.0±22.0 °C(Predicted)
• 密度：
  1.446±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  82.2
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-异硫氰基苯甲酸甲酯 在 sodium hydroxide 作用下， 以 various solvent(s) 为溶剂， 反应 90.16h， 生成 2-{[(1H)-pyrrole-2-carbonyl]amino}benzoic acid
  参考文献：
  名称：

  Synthesis of Derivatives of Pyrrole Using Methyl 2-Isothiocyanatobenzoate

  摘要：

  DOI：

  10.1055/s-1984-30735

文献信息

• [EN] PIPERIDINOBENZODIAZEPINE COMPOUNDS WITH ANTI PROLIFERATIVE ACTIVITY<br/>[FR] COMPOSÉS DE PIPÉRIDINOBENZODIAZÉPINE AYANT UNE ACTIVITÉ ANTI-PROLIFÉRATIVE
  申请人：FEMTOGENIX LTD

  公开号：WO2017032983A1

  公开（公告）日：2017-03-02

  The invention relates to pyrridinobenzodiazepines (PDDs) comprising three fused 6-7-6-membered rings linked to aromatic groups, and pharmaceutically acceptable salts thereof, which are useful as medicaments, such as anti-proliferative agents. PDDs may be represented by formula (I): and salts and solvates thereof, wherein the dotted lines indicates the optional presence of a double bond between one or more of Ci and C2, C2and C3, and C3and C4; R1 and R2 are substituent groups; R3 is selected from H, C1-12 alkyl and CH2Ph; R4is selected from phenyl and C5-9heteroaryl groups optionally substituted, with the proviso that the optionally substituted C5-9heteroaryl is not indolyl; R19is selected from H and (CH2)t-NR20R21; Yiis N or CH; Y2 is N or CH; and wherein at least one of Y1and Y2 is CH; p is o or1; X1 is a connecting group; L is a linker group; X2 is a connecting group or is absent; q is selected from o,1, 2, 3,4,5and 6; A is selected from: for each Ai group one of Y3and Y4is selected from N-R17,S and O; and the other of Y3and Y4is CH; and Y5is selected from CH, N, S and COH; for each A2group one of Y6and Y7is independently selected from N and CH; and the other of Y6and Y7is CH; R13, R14, R17, R2oand R2iare independently selected from H and C1-6alkyl; and either: (i) R5and R6together form a double bond; (ii) R5is H and R6is OH; or (iii) R5is H and R6is OC1-6alkyl; with the proviso that when p is o and A is Ai, then: (a) for at least one Ai group one of Y3and Y4is selected from S and O; or (b) for at least one Ai group Y5is S; or (c) R4is not pyrrolyl, imidazolyl, optionally substituted pyrrolyl or optionally substituted imidazolyl.

  该发明涉及含有与芳香族基团连接的三个融合的6-7-6环的吡啶苯二氮䓬（PDDs）及其药学上可接受的盐，这些化合物可用作药物，如抗增殖剂。 PDDs可以用公式（I）表示：及其盐和溶剂化合物，其中虚线表示Ci和C2，C2和C3以及C3和C4中的一个或多个之间的双键的可选存在；R1和R2是取代基；R3从H，C1-12烷基和CH2Ph中选择；R4从苯基和C5-9杂环基团中选择，可选择地取代，但有条件的是可选择地取代的C5-9杂环基团不是吲哚基；R19从H和（CH2）t-NR20R21中选择；Yi是N或CH；Y2是N或CH；其中Y1和Y2中至少一个是CH；p是o或1；X1是连接基团；L是连接基团；X2是连接基团或不存在；q从o，1，2，3，4，5和6中选择；A从以下中选择：对于每个Ai基团，Y3和Y4中的一个从N-R17，S和O中选择；另一个从CH中选择；Y5从CH，N，S和COH中选择；对于每个A2基团，Y6和Y7中的一个独立地从N和CH中选择；另一个是CH；R13，R14，R17，R2o和R2i独立地从H和C1-6烷基中选择；并且：（i）R5和R6一起形成双键；（ii）R5是H，R6是OH；或（iii）R5是H，R6是OC1-6烷基；但有条件的是当p是o且A是Ai时，那么：（a）对于至少一个Ai基团，Y3和Y4中的一个从S和O中选择；或（b）对于至少一个Ai基团，Y5是S；或（c）R4不是吡咯基，咪唑基，可选择地取代的吡咯基或可选择地取代的咪唑基。
• An expedient route to aromatic pyrrolo[2,1-c][1,4]benzodiazepines and a study of their reactivity
  作者：Frédéric Fabis、Jana Sopkova-de Oliveira Santos、Sandrine Fouchet-Jolivet、Sylvain Rault

  DOI：10.1016/s0040-4039(01)00957-1

  日期：2001.7

  2-Hydroxypyrrolo[2,1-c][1,4]benzodiazepines were aromatised in refluxing thionyl chloride into 11-chloropyrrolo[2,1-c][1,4]benzodiazepines in high yield. This aromatic system is doubly reactive towards nucleophiles leading to rearranged products such as iminobenzoxazines and quinazolines.

  2-羟基吡咯并[2,1- c ^ ] [1,4]苯并二氮杂类中在回流的亚硫酰氯为11个氯吡咯芳香烃[2,1- c ^ ] [1,4]高收率苯二氮。该芳族体系对亲核试剂具有双反应性，从而导致重排产物，如亚氨基苯并恶嗪和喹唑啉。
• Synthesis of novel benzo[<i>h</i>] [1,6]naphthyridines<i>via</i>a rearrangement of hexahydro-5<i>H</i>-pyrrolo [2,1 -<i>c</i>] [1,4]benzodiazepines
  作者：Antoine Hinschberger、Frédéric Fabis、Jana Sopkova-De Oliveira Santos、Sylvain Rault

  DOI：10.1002/jhet.5570400209

  日期：2003.3

  Heating of hexahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-2,5,11-trione in boiling phosphoryl chloride led to a rearranged product like 3,5-dichlorobenzo[h][1,6]naphthyridine. This structure was established from X-ray diffraction analysis.

  在沸腾的磷酰氯中加热六氢-5 H-吡咯并[ 2,1- c ] [1,4]苯并二氮杂-2,5,11-三酮导致重排产物，如3,5-二氯苯并[ h ] [1， 6]萘啶。通过X射线衍射分析确定该结构。
• LOONEY-DEAN, V.;LINDAMOOD, B. S.;PAPADOPOULOS, E. P., SYNTHESIS, BRD, 1984, N 1, 68-71
  作者：LOONEY-DEAN, V.、LINDAMOOD, B. S.、PAPADOPOULOS, E. P.

  DOI：——

  日期：——
• PIPERIDINOBENZODIAZEPINE COMPOUNDS WITH ANTI PROLIFERATIVE ACTIVITY
  申请人：Femtogenix Limited

  公开号：EP3337795A1

  公开（公告）日：2018-06-27