4-氧代嘧啶并[5,6-b]吲哚 | 61553-71-7

• 物质功能分类: 医药中间体 - 杂环化合物 - 嘧啶类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并嘧啶类
• 中文名称: 4-氧代嘧啶并[5,6-b]吲哚
• 英文名称: 5H-pyrimido<5,4-b>indole-4-one
• 英文别名: 5H-pyrimido[5,4-b]indol-4-one；3,5-dihydro-4H-pyrimido[5,4-b]indol-4-one；3H-4-Oxo-pyrimido<5,6-b>indol；3,5-dihydro-pyrimido[5,4-b]indol-4-one；2,9-dihydro-2,4,9-triaza-fluoren-1-one；3H-Pyrimido[5,4-b]indol-4(5H)-one；3,5-dihydropyrimido[5,4-b]indol-4-one
• CAS: 61553-71-7
• 化学式: C₁₀H₇N₃O
• mdl: MFCD01560663
• 分子量: 185.185
• InChiKey: SQKANMIJNAMTAQ-UHFFFAOYSA-N

物化性质

• 熔点：
  >350 °C(Solv: N,N-dimethylformamide (68-12-2))
• 沸点：
  526.4±23.0 °C(Predicted)
• 密度：
  1.55±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 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：
  57.2
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302

反应信息

• 作为反应物：
  描述：

  4-氧代嘧啶并[5,6-b]吲哚 在 tetraphosphorus decasulfide 作用下， 以 吡啶 为溶剂， 反应 6.0h， 以80%的产率得到4-mercapto-5H-pyrimido<5,4-b>indole
  参考文献：
  名称：

  4-肼基-5 H-嘧啶基[5,4- b ]吲哚的合成及相关化合物

  摘要：

  本文描述了两种4-氨基-5-的合成ħ嘧啶并[5,4- b ]吲哚5，4-肼基-5- ħ嘧啶并[5,4- b ]吲哚6中，两个1,2,4-三唑并[4，3- c ]嘧啶[5，4- b ]吲哚8和四唑并[ 4，5- c ]嘧啶[5，4- b ]吲哚10。从3-氨基吲哚-2-羧酸乙酯1开始，通过与甲酰胺缩合获得5 H-嘧啶基[5,4 - b ]吲哚-4-酮2（80％）。2的反应用三氯氧化磷和五硫化二磷分别制得4-氯-5 H-嘧啶并[5,4- b ]吲哚3（70％）和5 H-嘧啶并[5,4- b ]吲哚并4-硫酮4（80 ％）。化合物3与胺（吗啉，哌啶）反应生成相应的4-氨基-5 H-嘧啶[5,4- b ]-吲哚5，化合物4与肼反应生成4-肼基-5 H-嘧啶[ 5,4- b ]吲哚6（80％）。两个6（亚苄基，异亚丙基）7也准备了（9​​0％）。化合物6与甲酸和乙酸反应生成（65-75％）各自的1,2

  DOI：

  10.1002/jhet.5570230302
• 作为产物：
  描述：

  3-氨基-2-吲哚羧酸乙酯 以 formamide 为溶剂， 反应 2.0h， 以80%的产率得到4-氧代嘧啶并[5,6-b]吲哚
  参考文献：
  名称：

  4-肼基-5 H-嘧啶基[5,4- b ]吲哚的合成及相关化合物

  摘要：

  本文描述了两种4-氨基-5-的合成ħ嘧啶并[5,4- b ]吲哚5，4-肼基-5- ħ嘧啶并[5,4- b ]吲哚6中，两个1,2,4-三唑并[4，3- c ]嘧啶[5，4- b ]吲哚8和四唑并[ 4，5- c ]嘧啶[5，4- b ]吲哚10。从3-氨基吲哚-2-羧酸乙酯1开始，通过与甲酰胺缩合获得5 H-嘧啶基[5,4 - b ]吲哚-4-酮2（80％）。2的反应用三氯氧化磷和五硫化二磷分别制得4-氯-5 H-嘧啶并[5,4- b ]吲哚3（70％）和5 H-嘧啶并[5,4- b ]吲哚并4-硫酮4（80 ％）。化合物3与胺（吗啉，哌啶）反应生成相应的4-氨基-5 H-嘧啶[5,4- b ]-吲哚5，化合物4与肼反应生成4-肼基-5 H-嘧啶[ 5,4- b ]吲哚6（80％）。两个6（亚苄基，异亚丙基）7也准备了（9​​0％）。化合物6与甲酸和乙酸反应生成（65-75％）各自的1,2

  DOI：

  10.1002/jhet.5570230302

文献信息

• [EN] PYRROLOPYRIMIDINE DERIVATIVES AS MODULATORS OF MULTI-DRUG RESISTANCE (MDR)<br/>[FR] DERIVES PYRROLOPYRIMIDINIQUES CONVENANT COMME MODULATEURS DE LA MULTIRESISTANCE AUX MEDICAMENTS
  申请人：XENOVA LTD

  公开号：WO2004111052A1

  公开（公告）日：2004-12-23

  A compound which is a pyrrolopyrimidine of formula (I) wherein R1 is selected from H, Cl-C6 alkyl which is unsubstituted or substituted, (CH2)nAr1, (CH2)pNR4R5, halogen and (CH2)pX; R2 is CH2)pArl; R3 is selected from H, Cl -C6 alkyl which is unsubstituted or substituted, (CH2)pZ and (CH2)pArl; P is an unsaturated 5, 6, or 7 membered carbocyclic or heterocyclic ring which is unsubstituted or substituted; R4 and R5 which are the same or different are selected from H, Cl -C6 alkyl which is unsubstituted or substituted, (CH2)nC3-C10 cycloalkyl, (CH2)nAr1 , and (CH2)nOR6, or R4 and R5 together with the nitrogen atom to which they are attached, form a saturated five or six membered nitrogen containing heterocyclic ring which may contain one extra heteroatom selected from 0, N and S and which is unsubstituted or substituted; R6 is selected from H, Cl -C6 alkyl which is unsubstituted or substituted, C3-C10 cycloalkyl, (CH2)nOC1-C6alkyl which is unsubstituted or substituted, (CH2)nO(CH2)nAr1 , (CH2)nCO2C1-C6,alkyl which is unsubstituted or substituted and (CH2)nAr1; X is selected from CN, azide, (CH2)nNHSO2R6 and (CH2)nNHCOR6; Z is selected from CN, CO2R6 and CONR4R5; Ar1 is the same or different when more than one is present within a given substituent group and is an unsaturated C6-C10 membered carbocylic group or an unsaturated 5-11 membered heterocycle, either of which is unsubstituted or substituted; p is an integer of 1 to 6; n is the same or different when more than one is present within a given substituent group and is 0 or an integer of 1 to 6; with the proviso that the pyrrolepyrimidine compound of formula (I) is other than 1-(4-benzyl-piperazin-1-yl)-9H-2,4,9-triaza-fluorene; and the pharmaceutically acceptable salts thereof, have activity as inhibitors of MRP (multidrug resistant protein) and may thus be used to modulate multidrug resistance, for instance in potentiating the cytotoxicity of a chemotherapeutic agent.

  化合物是一种公式为（I）的吡咯吡嘧啶，其中R1从H、未取代或取代的Cl-C6烷基、（CH2）nAr1、（CH2）pNR4R5、卤素和（CH2）pX中选择；R2为（CH2）pArl；R3从H、未取代或取代的Cl-C6烷基、（CH2）pZ和（CH2）pArl中选择；P为未取代或取代的不饱和5、6或7成员碳环或杂环；R4和R5相同或不同，从H、未取代或取代的Cl-C6烷基、（CH2）nC3-C10环烷基、（CH2）nAr1和（CH2）nOR6中选择，或者R4和R5与它们连接的氮原子一起形成饱和的含氮五元或六元杂环，可能含有一个额外的杂原子，选择自O、N和S，未取代或取代；R6从H、未取代或取代的Cl-C6烷基、C3-C10环烷基、（CH2）nOC1-C6烷基、未取代或取代的（CH2）nO（CH2）nAr1、未取代或取代的（CH2）nCO2C1-C6烷基和（CH2）nAr1中选择；X从CN、叠氮、（CH2）nNHSO2R6和（CH2）nNHCOR6中选择；Z从CN、CO2R6和CONR4R5中选择；Ar1当多个存在于给定的取代基组内时相同或不同，为未取代或取代的不饱和C6-C10成员碳环或未取代或取代的不饱和5-11成员杂环；p为1至6的整数；n当多个存在于给定的取代基组内时相同或不同，为0或1至6的整数；但是，公式（I）的吡咯吡嘧啶化合物不是1-（4-苄基哌嗪-1-基）-9H-2,4,9-三氮杂萘；其药学上可接受的盐具有作为MRP（多药耐药蛋白）抑制剂的活性，因此可用于调节多药耐药性，例如在增强化疗药物的细胞毒性方面。
• Pyrrolopyrimidine derivatives and analogs and their use in the treatment and prevention of diseases
  申请人：Grotzfeld M. Robert

  公开号：US20050153989A1

  公开（公告）日：2005-07-14

  Described herein are compounds and compositions for modulating kinase activity, and methods for modulating kinase activity using the compounds and compositions. Also described herein are methods of using the compounds and/or compositions in the treatment and prevention of a variety of diseases and unwanted conditions in subjects.

  本文描述了用于调节激酶活性的化合物和组合物，以及使用这些化合物和组合物调节激酶活性的方法。本文还描述了在治疗和预防受试者中各种疾病和不良状况中使用这些化合物和/或组合物的方法。
• 含嘧啶或吡啶的稠环化合物及其作为抗肿瘤药 物的应用
  申请人：上海医药工业研究院

  公开号：CN104045642B

  公开（公告）日：2016-08-24

  本发明公开了一类含嘧啶或吡啶结构的稠环化合物及其作为抗肿瘤药物的应用，所述稠环化合物为具有如式（I）所示的化合物或其药学上可接受的盐；本发明的化合物，作为抗肿瘤药物应用时，具有更强的抗肿瘤活性和更小的毒副作用，更易于作为抗肿瘤药物使用。
• METHODS FOR SEPARATING CARBON NANOTUBES
  申请人：Papadimitrakopoulos Fotios

  公开号：US20100044230A1

  公开（公告）日：2010-02-25

  Disclosed herein too is a method that includes dispersing nanotubes in media that comprises flavin moieties substituted with solubilizing side chains, and/or non-flavin containing molecular species; self-assembling the flavin moieties and other non-flavin containing molecular species in a pattern that is orderly wrapped around the nanotubes to form a composite; introducing desired amounts of an optional reagent that competes with self-assembly in order to disturb the wrapping around nanotubes with moderate order; and centrifuging the mass of the nanotubes and the composites to extract the composite from other nanotubes that are not in composite form.

  本文还公开了一种方法，其中包括将纳米管分散在介质中，该介质包含用可溶性侧链取代的黄酮衍生物和/或非黄酮含量的分子物种；自组装黄酮衍生物和其他非黄酮含量的分子物种，以有序地缠绕在纳米管周围形成复合物；引入所需量的可选试剂，该试剂与自组装竞争，以扰乱中度有序的纳米管周围的缠绕；并离心纳米管和复合物的质量，以从未形成复合物的其他纳米管中提取复合物。
• 9-Deazapurines as Broad-Spectrum Inhibitors of the ABC Transport Proteins P-Glycoprotein, Multidrug Resistance-Associated Protein 1, and Breast Cancer Resistance Protein
  作者：Katja Stefan、Sven Marcel Schmitt、Michael Wiese

  DOI：10.1021/acs.jmedchem.7b00788

  日期：2017.11.9

  P-Glycoprotein (P-gp, ABCB1), multidrug resistance-associated protein 1 (MRP1, ABCC1), and breast cancer resistance protein (BCRP, ABCG2) are the three major ABC transport proteins conferring resistance to many structurally diverse anticancer agents, leading to the phenomenon called multidrug resistance (MDR). Much effort has been put into the development of clinically useful compounds to reverse MDR. Broad-spectrum inhibitors of ABC transport proteins can be of great use in cancers that simultaneously coexpress two or three transporters. In this work, we continued our effort to generate new, potent, nontoxic, and multiply effective inhibitors of the three major ABC transporters. The best compound was active in a very low micromolar concentration range against all three transporters and restored sensitivity toward daunorubicin (P-gp and MRP1) and SN-38 (BCRP) in A2780/ADR (P-gp), H69AR (MRP1), and MDCK II BCRP (BCRP) cells. Additionally, the compound is a noncompetitive inhibitor of daunorubicin (MRP1), calcein AM (P-gp), and pheophorbide A (BCRP) transport.