R-1-(5-quinolinyloxy)-2,3-epoxypropane | 129717-21-1

• 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: R-1-(5-quinolinyloxy)-2,3-epoxypropane
• 英文别名: 1-(5-quinolinyloxy)-2,3-epoxypropane；5-(2,3-epoxypropoxy)quinoline；5-oxiranylmethoxy-quinoline；5-(Oxiran-2-ylmethoxy)quinoline
• CAS: 129717-21-1
• 化学式: C₁₂H₁₁NO₂
• 分子量: 201.225
• InChiKey: MMRYHBTWIHLITG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  34.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2,2-二苯基乙酰基)哌嗪 、 R-1-(5-quinolinyloxy)-2,3-epoxypropane 以 异丙醇 为溶剂， 反应 4.0h， 以70%的产率得到1-[4-[2-羟基-3-(5-喹啉基氧基)丙基]-1-哌嗪基]-2,2-二苯基乙酮
  参考文献：
  名称：

  新合成的喹啉衍生物的结构-活性关系用于逆转癌症中的多药耐药性。

  摘要：

  在体外检查了24种新合成的喹啉衍生物对肿瘤细胞多药耐药性（MDR）的影响。在低浓度下，这些化合物增强了[3H]长春新碱在K562 / ADM细胞中的积累，并逆转了肿瘤细胞MDR。结构-活性关系分析的结果表明，在高活性化合物中，疏水部分的两个芳基环偏离同一平面，因此它们能够与P-170糖蛋白（P-gp）的氢键供体相互作用pi-氢-pi相互作用。影响这些化合物的MDR-逆转活性的其他主要结构特征是哌嗪中的喹啉氮原子和碱性氮原子。此外，在高活性化合物中

  DOI：

  10.1021/jm960869l
• 作为产物：
  描述：

  司维拉姆杂质 在 caesium carbonate 作用下， 以 丙酮 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 R-1-(5-quinolinyloxy)-2,3-epoxypropane
  参考文献：
  名称：

  [DE] VERFAHREN ZUR HERSTELLUNG VON REINSTEM RAC-1-{4-[2-HYDROXY-3-(5-QUINOLYLOXY)PROPYL] PIPERAZIN-1-YL}-2,2-DIPHENYLETHAN-1-ONE FUMARAT UND REINSTES RAC-1-{4-[2-HYDROXY-3-(5-QUINOLYLOXY)PROPYL]PIPERAZIN-1-YL}-2,2-DIPHENYLETHAN-1-ONE
  [EN] METHOD FOR PRODUCING THE PUREST RAC-1-{4-[2-HYDROXY-3-(5-QUINOLYLOXY)PROPYL] PIPERAZIN-1-YL}-2,2-DIPHENYLETHAN-1-ONE FUMARATE AND THE PUREST RAC-1-{4-[2-HYDROXY-3-(5-QUINOLYLOXY)PROPYL]PIPERAZIN-1-YL}-2,2-DIPHENYLETHAN-1-ONE FUMARATE
  [FR] PROCEDE DE PRODUCTION DE FUMARATE ULTRAPUR DE RAC-1-{4-[2-HYDROXY-3-(5-QUINOLYLOXY)PROPYL]-PIPERAZINE-1-YLE}2,2-DIPHENYLETHANE-1-ONE ET FUMARATE ULTRAPUR DE RAC-1-{4-[2-HYDROXY-3-(5-QUINOLYLOXY)PROPYL]-PIPERAZINE-1-YLE}2,2-DIPHENYLETHANE-1-ONE

  摘要：

  这项技术描述了一种制备最纯的富马酸盐rac-1-{4-[2-羟基-3-(5-喹诺氧基)丙基]-哌嗪-1-基}-2,2-二苯乙酮以及富马酸盐rac-1-{4-[2-羟基-3-(5-喹诺氧基)丙基]哌嗪-1-基}-2,2-二苯乙酮，其纯度至少为98.55%。

  公开号：

  WO2004099151A1

文献信息

• Quinoline derivatives
  申请人：Mitsui Toatsu Chemicals, Incorporated

  公开号：US05112817A1

  公开（公告）日：1992-05-12

  Novel heterocyclic compounds, which are represented by the following general formula, useful as anticancer drug potentiaters having a potentiating effect on the incorporation of anticancer drugs into cancer cells, the compounds each synthesized by, for example, reacting a epoxy compound obtained by reacting a heterocyclic compound with an epihalogenohydrin, with an amine derivative.

  新颖的杂环化合物，以以下通用公式表示，作为抗癌药物增效剂，对抗癌药物的纳入癌细胞具有增效作用，这些化合物通过例如将由异环化合物与环氧卤水合物反应得到的环氧化合物与胺衍生物反应合成。
• [EN] PYRROLOPYRIMIDINE DERIVATIVES USEFUL AS MODULATORS OF MULTIDRUG RESISTANCE<br/>[FR] DERIVES DE PYRROLOPYRIMIDINE POUVANT ETRE UTILISES EN TANT QUE MODULATEURS DE LA MULTIRESISTANCE AUX MEDICAMENTS
  申请人：XENOVA LTD

  公开号：WO2004065389A1

  公开（公告）日：2004-08-05

  A compound which is a pyrrolopyrimidine of formula (I) wherein: R1 is selected from R9 and halogen; R2 is NR6R7; R3 is selected from H, C1-C6 alkyl which is unsubstituted or substituted and -(CH2) nAr; R4 is selected from H, C1-C6 alkyl and -(CH2)„ Ar; or R3 and R4 form, together with the N and C atoms to which they are attached, a fused five-, six-, seven- or eight-membered N-containing saturated ring which is unsubstituted or substituted; R5 is selected from CN, C02R9, C(O)NR10R11, -(CH2)nOH, -(CH2)nR10Rn, -C=CH, -C(S)NR10R11, -C(NH2)=NOR9, -C(R9)=NOR9, -C(NH2)NH, -C(O)R9 and an unsaturated 5- or 6-membered heterocyclic group which contains 1, 2 or 3 heteroatoms selected from N, O and S and which is unsubstituted or substituted; R6 and R7, which are the same or different, are selected from C1-C6 alkyl which is unsubstituted or substituted, -(CH2)nX and -(CH2)nAr; or R6 and R7 form, together with the nitrogen atom to which they are attached, a saturated five-, six-, seven- or eight-membered heterocyclic group which contains one nitrogen atom and 0 or from 1 to 3 additional heteroatoms selected from N, O and S, which is unsubstituted or substituted and which optionally contains one or two bridgehead atoms; R10 and R11, which are the same or different, are selected from H, C1-C6 alkyl which is unsubstituted or substituted, -(CH2)nC3-C10 cycloalkyl and -(CH2) nAr; or R10 and R11 form, together with the nitrogen atom to which they are attached, a saturated five or six membered heterocyclic group which contains a nitrogen atom and 0 or from to 3 additional heteroatoms selected from O, S and N, which is unsubstituted or substituted and which is optionally fused to a benzene ring which is unsubstituted or substituted; n is the same or different when more than one is present within a given substituent group and is 0 or an integer of from 1 to 6; X is selected from -CN, -C02R9 and -NR10R11; R9 is the same or different when more than one is present within a given substituent group and is selected from -H, -QAr, -(CH2) nAr, C1-C6 alkyl which is unsubstituted or substituted and -(CH2) nC3-C10cycloalkyl, wherein the cycloalkyl moiety is optionally fused to a benzene ring which is unsubstituted or substituted; Q is C2-C6 alkenylene or alkynylene; and Ar is an unsaturated C6-C10 membered carbocyclic group or an unsaturated 5-11 membered heterocyclic group, which groups are unsubstituted or substituted; or a pharmaceutically acceptable salt thereof. These compounds 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.

  一种具有以下结构式(I)的吡咯吡嘧啶化合物，其中：R1从R9和卤素中选择；R2为NR6R7；R3从H、未取代或取代的C1-C6烷基和-(CH2) nAr中选择；R4从H、C1-C6烷基和-( ) nAr中选择；或者R3和R4与它们连接的N和C原子一起形成未取代或取代的融合的含氮饱和环，该环为五、六、七或八元环；R5从CN、C02R9、C(O)NR10R11、-( )nOH、-( )nR10Rn、-C=CH、-C(S)NR10R11、-C(NH2)=NOR9、-C(R9)=NOR9、-C(NH2)NH、-C(O)R9和一个含有1、2或3个异原子（N、O和S）且未取代或取代的不饱和5-或6元杂环基中选择；R6和R7相同或不同，从未取代或取代的C1-C6烷基、-( )nX和-( )nAr中选择；或者R6和R7与它们连接的氮原子一起形成含有一个氮原子和0或1至3个额外异原子（N、O和S）的饱和五、六、七或八元杂环基，该环未取代或取代，可选地包含一个或两个桥头原子；R10和R11相同或不同，从未取代或取代的H、C1-C6烷基、-( )nC3-C10环烷基和-( )nAr中选择；或者R10和R11与它们连接的氮原子一起形成含有一个氮原子和0或1至3个额外异原子（O、S和N）的饱和五或六元杂环基，该环未取代或取代，可选地与未取代或取代的苯环融合；n在给定取代基中的多个存在时相同或不同，为0或1至6的整数；X从-CN、-C02R9和-NR10R11中选择；R9在给定取代基中的多个存在时相同或不同，从-H、-QAr、-( )nAr、未取代或取代的C1-C6烷基和-( )nC3-C10环烷基中选择，其中环烷基部分可选地与未取代或取代的苯环融合；Q为C2-C6烯基或炔基；Ar为未取代或取代的不饱和C6-C10环烷基或不饱和5-11元杂环基，或其药学上可接受的盐。这些化合物具有作为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，例如增强化疗药物的细胞毒性。
• Quinoline derivative fumarates
  申请人：Mitsui Toatsu Chemicals, Incorporated

  公开号：US05434155A1

  公开（公告）日：1995-07-18

  Compounds having an activity to stimulate the carcinostatic effect of carcinostatic agents, which can be expressed by the following general formula (1): ##STR1## in which A is ##STR2## (in which R.sub.1, R.sub.2 and R.sub.3 are each independent and represent a hydrogen atom or a phenyl group) are made into fumarates so as to improve their oral absorbability and solubility in water without interfering with their effects.

  具有刺激癌抑制剂的抗癌效果活性的化合物，可以通过以下一般公式（1）表示：##STR1## 其中A是##STR2## （其中R.sub.1、R.sub.2和R.sub.3各自独立地代表氢原子或苯基）被制成富马酸盐，以改善其口服吸收性和水溶性，而不会干扰其效果。
• BRIDGED ARYL PIPERAZINES DERIVATIVES USEFUL FOR THE TREATMENT OF CNS, GI-URINARY AND REPRODUCTIVE DISORDERS
  申请人：Creighton J. Christopher

  公开号：US20080070919A1

  公开（公告）日：2008-03-20

  The present invention is directed to bridged aryl piperazine derivatives, pharmaceutical compositions containing them and their use in the treatment of depression and related disorders. The compounds of the present invention are serotonin transport inhibitors and/or modulators of 5HT 1A .

  本发明涉及桥联芳基哌嗪衍生物，含有它们的药物组合物以及它们在治疗抑郁症和相关疾病中的用途。本发明的化合物是血清素转运抑制剂和/或5HT1A的调节剂。
• [EN] 10,11-METHANODIBENZOSUBERANE DERIVATIVES USED AS CHEMOSENSITIZING AGENTS<br/>[FR] DERIVES DE 10,11-METHANODIBENZOSUBERANE UTILISES COMME AGENTS DE CHIMIOSENSIBILISATION
  申请人：SYNTEX (U.S.A.) INC.

  公开号：WO1994024107A1

  公开（公告）日：1994-10-27

  (EN) 10,11-Methanodibenzosuberane derivatives, i.e., the compounds of formula (I), wherein A is -CH2-CH2-, -CH2-CHRa-CH2-, or -CH2-CHRa-CHRb-CH2-, where one of Ra or Rb is H, OH, or lower acyloxy, and the other is H; R1 is H, F, Cl or Br; R2 is H, F, Cl or Br; and R3 is heteroaryl or phenyl optionally substituted with F, Cl, Br, CF3, CN, NO2 or OCHF2; and the pharmaceutically acceptable salts thereof, are useful chemosensitizing agents, e.g., for cancer chemotherapy, particularly for treating multidrug resistance.(FR) L'invention se rapporte à des dérivés de 10,11-méthanodibenzosubérane, qui sont des composés représentés par la formule (I), où A représente -CH2-CH2-, -CH2-CHRa-CH2-, ou -CH2-CHRa-CHRb-CH2-, où l'un des éléments Ra ou Rb représente H, OH ou acyloxy inférieur, et l'autre représente H; R1 représente H, F, Cl ou Br; R2 représente H, F, Cl ou Br; et R3 représente hétéroaryle ou phényle éventuellement substitué par F, Cl, Br, CF3, CN, NO2 ou OCHF2; ainsi qu'aux sels pharmaceutiquement acceptables de ces dérivés, lesquels sont utiles comme agents de chimiosensibilisation, par exemple dans la chimiothérapie contre le cancer, notamment pour traiter la résistance multiple aux anticancéreux.

  10,11-甲烷二苯基戊烷衍生物，即公式（I）中的化合物，其中A为-CH2- -，- -CHRa- -或- -CHRa-CHRb- -，其中Ra或Rb中的一个为H，OH或较低的酰氧基，另一个为H; R1为H，F，Cl或Br; R2为H，F，Cl或Br; R3为杂环芳基或苯基，可选地取代为F，Cl，Br，CF3，CN，NO2或OCHF2;以及其药学上可接受的盐，是有用的化疗增敏剂，例如用于癌症化疗，特别是用于治疗多药耐药。