6-amino-3-(4-(4-(4-fluorophenyl)piperazin-1-yl)butyl)benzo[d]oxazol-2(3H)-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 6-amino-3-(4-(4-(4-fluorophenyl)piperazin-1-yl)butyl)benzo[d]oxazol-2(3H)-one
• 英文别名: 6-Amino-3-[4-[4-(4-fluorophenyl)piperazin-1-yl]butyl]-1,3-benzoxazol-2-one
• 化学式: C₂₁H₂₅FN₄O₂
• 分子量: 384.454
• InChiKey: NTEIKGNKDLPTSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  62
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  硫光气 、 6-amino-3-(4-(4-(4-fluorophenyl)piperazin-1-yl)butyl)benzo[d]oxazol-2(3H)-one 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 91.0h， 以53%的产率得到1,3-bis(3-(4-(4-(4-fluorophenyl)piperazin-1-yl)butyl)-2-oxo-2,3-dihydrobenzo[d]oxazol-6-yl)thiourea
  参考文献：
  名称：

  MAM03055A 的鉴定和表征：一种具有细胞毒活性的新型二价 sigma-2 受体/TMEM97 配体

  摘要：

  与正常细胞相比，Sigma-2 受体/跨膜蛋白 97 (TMEM97) 在癌细胞中上调。传统的 sigma-2 受体激动剂诱导细胞凋亡和自噬，使其在癌症治疗中受到关注。最近，我们报道了 sigma-2 受体的一种新的代谢刺激功能，显示 3-(4,5 二甲基噻唑-2-基)-2,5-二苯基溴化四唑 (MTT) 减少和糖酵解标志的刺激增加。6-典型 sigma-2 受体拮抗剂的取代类似物，6-乙酰基-3-(4-(4-(4-氟苯基)哌嗪-1-基)丁基)苯并[ d ]恶唑-2(3 H )-一个（SN79），产生代谢刺激和细胞毒性作用。在这里，我们比较了两种相关化合物的活性：6-氨基-3-(4-(4-(4-氟苯基)哌嗪-1-基)丁基)苯并[ d]oxazol-2(3 H )-one (CM571)，SN79 的 6-氨基衍生物，与 sigma-1 和 sigma-2 受体以及 1,3-bis(3-(4-

  DOI：

  10.1016/j.ejphar.2021.174263

文献信息

• HIGHLY SELECTIVE SIGMA RECEPTOR RADIOLIGANDS
  申请人：McCurdy Christopher R.

  公开号：US20110280804A1

  公开（公告）日：2011-11-17

  Compounds having the general formula III′, or IV′ wherein R 1 can be a radical of an optionally substituted C-4 to C-7 N-containing heterocycle or a radical of an optionally substituted cyclic or acyclic tertiary amine or isoindoline-1,3-dione: R 2,4,5,6 can each independently be any one or combinations of the following moieties, cyano, nitro, acyl, alkyl, amido, azido, isothiocyanate, isocyanate, optionally substituted anilino, halogens, ethers, sulfonamides, thioacyl, nitro, aromatic, heterocyclic, olefinic, acetylene, deuterium, or tritium; Y is S; Z can be either H, O, S, S—R or NR where R groups can be either H, aryls, alkyls, or cycloalkyls; “n” can be 1 to 5 carbons in length and stereoisomers, functional analogs, and pharmaceutically acceptable salts thereof and wherein the moiety bridging R 1 and N can be a substituted alkylene, optionally substituted alkenylene or optionally substituted alkynylene and where the alkylene group can include an inserted C 3 -C 5 cycloalkyl group, aromatic, and heterocyclic group; and wherein X is C 1 -C 4 radiohaloalkyl.

  具有通式III'或IV'的化合物，其中R1可以是一个可选取代的C-4到C-7含氮杂环的基团，或者是一个可选取代的环状或非环状三级胺或异吲哚啉-1,3-二酮的基团；R2、4、5、6可以各自独立地是以下任何一种或组合：氰基、硝基、酰基、烷基、酰胺基、偶氮基、异硫氰酸酯基、异氰酸酯基、可选取代的苯胺基、卤素、醚、磺酰胺基、硫代酰基、芳香族、杂环、烯烃、乙炔、氘或氚；Y是S；Z可以是H、O、S、S-R或NR，其中R基团可以是H、芳基、烷基或环烷基；“n”可以是1到5个碳原子，包括立体异构体、功能类似物和药物可接受的盐；其中桥接R1和N的基团可以是取代的烷基、可选取代的烯基或可选取代的炔基，其中烷基可以包括插入的C3-C5环烷基、芳香族和杂环基团；X为C1-C4放射性卤代烷基。
• HIGHLY SELECTIVE SIGMA RECEPTOR LIGANDS AND RADIOLIGANDS AS PROBES IN NOCICEPTIVE PROCESSING AND THE PATHPHYSIOLOGICAL STUDY OF MEMORY DEFICITS AND COGNITIVE DISORDERS
  申请人：The Board of Trustees of the Leland Stanford Junior University

  公开号：US20140328755A1

  公开（公告）日：2014-11-06

  A method for localizing and quantifying S1R role in nociceptive processing; for providing a guide to providing an analgesic therapy; of using an S1R selective ligand as a biomarker for pathphysiological study of memory deficits and cognitive disorders; or of detecting increased S1R density at the site of nerve injury arising from neuropathic pain comprising using as a probe at least one SR1 selective compound or radioligand of the general formula III′, or IV′:

  一种定位和量化S1R在伤害处理中的作用的方法；为提供镇痛疗法提供指导；使用S1R选择性配体作为记忆缺陷和认知障碍的病理生理研究的生物标志物；或者使用至少一种SR1选择性化合物或放射性配体作为探针，检测神经病理性疼痛引起的神经损伤部位的S1R密度增加，其化学结构为通式III'或IV'。
• HIGHLY SELECTIVE SIGMA 1 RECEPTOR LIGANDS AND RADIOLIGANDS AS PROBES IN NOCICEPTIVE PROCESSING AND THE PATHOPHYSIOLOGICAL STUDY OF MEMORY DEFICITS AND COGNITIVE DISORDERS
  申请人：The University Of Mississippi

  公开号：EP3102204B1

  公开（公告）日：2021-05-05
• HIGHLY SELECTIVE SIGMA RECEPTOR LIGANDS
  申请人：McCurdy Christopher R.

  公开号：US20100329978A1

  公开（公告）日：2010-12-30

  Compounds having the general formula II, III, or IV wherein R 1 can be a radical of an optionally substituted C-4 to C-7 N-containing heterocycle or a radical of an optionally substituted cyclic or acyclic tertiary amine or isoindoline-1,3-dione: R 2,3,4,5,6 can each independently be any one or combinations of the following moieties, cyano, nitro, acyl, alkyl, amido, azido, isothiocyanate, isocyanate, optionally substituted anilino, halogens, ethers, sulfonamides, thioacyl, nitro, aromatic, heterocyclic, olefinic, acetylene, deuterium, or tritium; Y can be either CH, CH 2 , O, S, OCH 2 , N—R, N—Ar, C—R, C—Ar; Z can be either H, O, S, S—R or NR. R groups can be either H, aryls, alkyls, or cycloalkyls; “n” can be 1 to 5 carbons in length and stereoisomers, functional analogs, and pharmaceutically acceptable salts thereof and wherein the moiety bridging R 1 and N can be a substituted alkylene, optionally substituted alkenylene or optionally substituted alkynylene and where the alkylene group can include an inserted C 3 -C 5 cycloalkyl group, aromatic, and hetercocyclic group; wherein X′ is halogen, or C 1 -C 4 haloalyl; wherein the R x is a C 1 -C 5 straight chain or branched chain alkyl or a C 1 -C 4 straight chain or branched chain haloalkyl.
• US8809381B2
  申请人：——

  公开号：US8809381B2

  公开（公告）日：2014-08-19