3-amino-4-chromanone hydrochloride

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 3-amino-4-chromanone hydrochloride
• 英文别名: 3-aminochroman-4-one hydrochloride；(4-Oxo-2,3-dihydrochromen-3-yl)azanium;chloride
• 化学式: C₉H₉NO₂*ClH
• mdl: MFCD20483363
• 分子量: 199.637
• InChiKey: YUWWVDYPEZGAEW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.49
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  52.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-amino-4-chromanone hydrochloride 在 10percent Pd/C lithium aluminium tetrahydride 、 氢气 、 三乙胺 作用下， 以 乙醚 、 乙醇 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 3-(N-n-propyl-N-propionylamino)-3,4-dihydro-2H-[1]benzopyran
  参考文献：
  名称：

  Thiazoloindans and Thiazolobenzopyrans:  A Novel Class of Orally Active Central Dopamine (Partial) Agonists

  摘要：

  The 2-aminothiazole moiety has proven its value in medicinal chemistry as a stable and lipophilic bioisosteric replacement of a phenol group. This approach has provided dopamine (DA) agonists with good oral availability. To further explore its use in the development of DA agonists, we have combined the 2-aminothiazole moiety with 2-aminoindans and 3-aminobenzopyrans, which are known templates for DA agonists. In this study we have synthesized 6-amino-3-(N,N-di-n-propylamino)-3,4-dihydro-2H-thiazole[5,4-f]-[1]benzopyran (12) and 6-amino-2-(N,N-di-n-propylamino)thiazolo[4,5-f]indan (20) and several analogues (13, 17, and 21). The affinity of the thiazolobenzopyrans and thiazoloindans for DA receptors was evaluated, which revealed compound 20 to have high affinity for DA DQ receptors. In addition, the compounds were screened for their potential to inhibit lipid peroxidation, to determine their radical scavenging properties. Compounds 12, 20, and 21 were subjected to further pharmacological evaluation in a functional assay to determine intrinsic activity. Compound 20 was also studied with microdialysis (to determine effects on DA turnover in striatum) and in unilaterally 6-OH-DA lesioned rats (to determine their potential as DA agonists). These studies selected compound 20 (GMC 1111) as particularly interesting. Compound 20 caused a rotation activation in unilaterally B-OH-DA lesioned rats and an increase in DA turnover in rat striatum. This dual agonist/antagonist action is best accounted for by its partial agonism at striatal DA D-2 receptors. Interestingly, 20 displayed long-lasting activity and excellent oral availability in B-OH-DA lesioned rats, making this compound potentially useful for the treatment of Parkinson's disease.

  DOI：

  10.1021/jm000087z
• 作为产物：
  描述：

  3-苯氧基丙腈 在 吡啶 、 盐酸 、 alpha-(1-氨基乙基)-苯甲醇 、 盐酸羟胺 、 sodium 、 甲苯 作用下， 以 甲醇 、 水 为溶剂， 反应 22.5h， 生成 3-amino-4-chromanone hydrochloride
  参考文献：
  名称：

  双位苯并吡喃吗啉类似物作为选择性多巴胺 D3 受体配体作为抗毒瘾治疗剂的设计、合成和初步生物活性评估

  摘要：

  三个系列的双位苯并吡喃吗啉类似物被设计、合成和评估为多巴胺 D3 受体的一类新型选择性配体。使用放射性配体结合测定法测定目标化合物的结合亲和力。大多数化合物对 D3 受体表现出相当大的结合亲和力和选择性。此外，还筛选了这些化合物在动物行为模型中缓解阿片类药物成瘾戒断症状的能力。结果表明，化合物20h对D3R表现出纳摩尔亲和力，并在纳洛酮诱导的吗啡依赖小鼠戒断症状动物模型中表现出抗毒瘾功效。

  DOI：

  10.1016/j.bmcl.2021.128269

文献信息

• Catalytic Asymmetric Aziridination of Enol Derivatives in the Presence of Chiral Copper Complexes to give Optically Active α-Amino Ketones
  作者：Waldemar Adam、Konrad Johann Roschmann、Chantu Ranjan Saha-Möller

  DOI：10.1002/(sici)1099-0690(200002)2000:3<557::aid-ejoc557>3.0.co;2-b

  日期：2000.2

  A series of acyclic and cyclic enol derivatives 1 has been transformed into the corresponding α-amino-functionalized ketones 2 by means of enantioselective catalytic aziridination with chiral Cu complexes, prepared in situ from [Cu(MeCN)4]PF6 and the optically active ligands 3, by using (N-tosylimino)iodobenzene (PhINTs) as a nitrogen source. The best enantioselectivities (ee values of up to 52%) have

  一系列无环和环状烯醇衍生物 1 已通过与手性 Cu 配合物的对映选择性催化氮丙啶化反应转化为相应的 α-氨基官能化酮 2，由 [Cu(MeCN)4]PF6 和光学活性配体原位制备3，通过使用（N-甲苯磺胺基）碘苯（PhINTs）作为氮源。电子失活的烯醇乙酸酯 1aδ 已经实现了最佳的对映选择性（ee 值高达 52%），但空间体积的引入和烯醇双键处的取代模式并没有提高 ee 值。与它们的无环对应物（完全消耗）相比，环状底物的反应要慢得多（仅高达 45% 的转化率）。
• [EN] MGLUR7 AGONIST COMPOUNDS FOR TREATING MGLUR7- REGULATED DISEASES, DISORDERS, OR CONDITIONS<br/>[FR] COMPOSÉS AGONISTES DE MGLUR7 POUR LE TRAITEMENT DE MALADIES, TROUBLES OU ÉTATS RÉGULÉS PAR MGLUR7
  申请人：TAKEDA PHARMACEUTICALS CO

  公开号：WO2018092921A1

  公开（公告）日：2018-05-24

  The present invention provides compounds of formula (I) and pharmaceutically acceptable salts thereof wherein Z, R1, R2, R3, R4, R5 and R6 are as defined in the specification, a process for their preparation, pharmaceutical compositions containing them and their use in therapy. The present invention further provides methods of treating at least one disease, disorder, or condition associated with the glutamatergic and GABAergic signalling pathways regulated in full or in part by metabotropic glutamate receptor 7 (mGluR7) by administering a compound of formula (I) or a pharmaceutically acceptable salt thereof to a subject. The compound may be a selective agonist of mGluR7, which modulates the release of at least one neurotransmitter in the subject.

  本发明提供了式(I)的化合物及其药用盐，其中Z、R1、R2、R3、R4、R5和R6如规范中定义，以及它们的制备方法，含有它们的药物组合物以及它们在治疗中的用途。本发明还提供了治疗至少一种与谷氨酸能和GABA能信号通路相关的疾病、紊乱或症状的方法，该信号通路完全或部分由代谢型谷氨酸受体7（mGluR7）调节，通过向受试者投药式(I)的化合物或其药用盐。该化合物可能是mGluR7的选择性激动剂，调节受试者中至少一种神经递质的释放。
• 2-(CYCLIC AMINO)-PYRIMIDONE DERIVATIVES
  申请人：Fukunaga Kenji

  公开号：US20090233918A1

  公开（公告）日：2009-09-17

  A compound represented by the formula (I), an optically active isomer thereof, or a pharmaceutical acceptable salt thereof: wherein R 2 represents a hydrogen or the like; R 3 represents methyl group or the like; R 20 represents a halogen atom or the like; q represents an integer of 0 to 3; Z represent nitrogen atom, CH, or the like; R 4 represents hydrogen or the like; R 5 represents hydrogen or the like; R 6 represents a substituted alkyloxy and the like; p represents an integer of 0 to 3; X represents bond, CH 2 , oxygen atom, NH, or the like; any one or more of R 5 and R 6 , R 5 and R 4 , R 6 and R 4 , X and R 5 , X and R 4 , X and R 6 , and R 6 and R 6 may combine to each other to form a ring, which is used for preventive and/or therapeutic treatment of a disease caused by tau protein kinase 1 hyperactivity such as a neurodegenerative diseases (e.g. Alzheimer disease).

  化合物的化学式为（I），其手性异构体或药物可接受的盐：其中，R2代表氢或类似物；R3代表甲基基团或类似物；R20代表卤素原子或类似物；q表示0到3的整数；Z代表氮原子，CH或类似物；R4代表氢或类似物；R5代表氢或类似物；R6代表取代的烷氧基或类似物；p表示0到3的整数；X代表键，CH2，氧原子，NH或类似物；R5和R6，R5和R4，R6和R4，X和R5，X和R4，X和R6以及R6和R6中的任何一个或多个可以结合形成环，用于预防和/或治疗由tau蛋白激酶1过度活化引起的疾病，例如神经退行性疾病（例如阿尔茨海默病）。
• 2-(cyclic amino)-pyrimidone derivatives
  申请人：Fukunaga Kenji

  公开号：US08569294B2

  公开（公告）日：2013-10-29

  A compound represented by the formula (I), an optically active isomer thereof, or a pharmaceutical acceptable salt thereof: wherein R2 represents a hydrogen or the like; R3 represents methyl group or the like; R20 represents a halogen atom or the like; q represents an integer of 0 to 3; Z represent nitrogen atom, CH, or the like; R4 represents hydrogen or the like; R5 represents hydrogen or the like; R6 represents a substituted alkyloxy and the like; p represents an integer of 0 to 3; X represents bond, CH2, oxygen atom, NH, or the like; any one or more of R5 and R6, R5 and R4, R6 and R4, X and R5, X and R4, X and R6, and R6 and R6 may combine to each other to form a ring, which is used for preventive and/or therapeutic treatment of a disease caused by tau protein kinase 1 hyperactivity such as a neurodegenerative diseases (e.g. Alzheimer disease).

  化合物的化学式为（I），其手性异构体或其药学上可接受的盐：其中，R2代表氢或类似物；R3代表甲基基团或类似物；R20代表卤素原子或类似物；q代表0到3的整数；Z代表氮原子，CH或类似物；R4代表氢或类似物；R5代表氢或类似物；R6代表取代的烷氧基或类似物；p代表0到3的整数；X代表键，CH2，氧原子，NH或类似物；R5和R6，R5和R4，R6和R4，X和R5，X和R4，X和R6以及R6和R6中的任意一个或多个可以相互组合形成环，用于预防和/或治疗由tau蛋白激酶1过度活化引起的疾病，例如神经退行性疾病（例如阿尔茨海默病）。
• Antiinflammatory and/or analgesic 3,4-dihydro(or 1,4-dihydro)-2-((substituted)thiol)-(1)-benzopyrano(3,4-d)imidazoles and their corresponding sulfoxides and sulfones
  申请人：E.I. DU PONT DE NEMOURS AND COMPANY

  公开号：EP0057932A1

  公开（公告）日：1982-08-18

  3,4-Dihydro(or 1,4-dihydro)-2-[(substituted)-thio]-[1]-benzopyrano[3,4-d]imidazoles and their corresponding sulfoxides and sulfones, such as 3,4-dihydro-(or 1,4-dihydro)-4-phenyl-2-[(1,1,2,2-tetrafluoroethyl)sulfonyl]-[1]benzopyrano[3,4-d]imidazole, are useful in the treatment of inflammation and/or pain.

  3,4-二氢（或 1,4-二氢）-2-[（取代）-硫代]-[1]-苯并吡喃并[3,4-d]咪唑及其相应的亚砜和砜，如 3,4-二氢-（或 1、4-苯基-2-[(1,1,2,2-四氟乙基)磺酰基]-[1]苯并吡喃并[3,4-d]咪唑，可用于治疗炎症和/或疼痛。