1-(4-(methylsulfonyl)phenyl)ethanamine hydrochloride | 98959-90-1

• 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: 1-(4-(methylsulfonyl)phenyl)ethanamine hydrochloride
• 英文别名: 1-(4-(methylsulfonyl)phenyl)ethan-1-amine hydrochloride；1-(4-(methylsulfonyl)phenyl)ethanaminium hydrochloride；1-(4-methanesulfonyl-phenyl)-ethylamine; hydrochloride；1-(4-Methansulfonyl-phenyl)-aethylamin; Hydrochlorid；1-(4-methylsulfonylphenyl)ethylazanium;chloride
• CAS: 98959-90-1
• 化学式: C₉H₁₃NO₂S*ClH
• mdl: MFCD07686078
• 分子量: 235.735
• InChiKey: JAECXGZNWPVNEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.36
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  68.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-(methylsulfonyl)phenyl)ethanamine hydrochloride 、 8-溴-3-甲基-[1,6]萘啶-2-羧酸 在 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.03h， 以94%的产率得到8-bromo-N-(1-(4-(methylsulfonyl)phenyl)ethyl)-1,6-naphthyridine-2-carboxamide
  参考文献：
  名称：

  [EN] SUBSTITUTED 1,6-NAPHTHYRIDINES
  [FR] 1,6-NAPHTYRIDINES SUBSTITUÉES

  摘要：

  本发明涉及使用一般式（I）的化合物，其中R'是氢或较低的烷基；R1是卤素、较低的烷基、环烷基或氰基；或者是苯基，可选择地被一个到三个取代基取代，所述取代基选自较低的烷基、被卤素取代的较低烷基、较低的烷氧基、被卤素取代的较低烷氧基、卤素、氰基、羟基、C(O)-NH-较低烷基、CH2-C(O)-NH-较低烷基、CH2-NH-C(O)-较低烷基、CH2NH2、S(O)2CH3、S(O)2N(CH3)2，或者是由杂环烷基组成的基团；或者是吡唑-1、4或5-基，可选择地被较低烷基取代；或者是噻唑-5-基，可选择地被一个或两个较低烷基基团取代；或者是吡啶-2、3或4-基，可选择地被较低烷基、较低烷氧基、卤素或N(CH3)2取代；或者是3,6-二氢-2H-吡喃；或者是苯并[d][1,3]二噁嗪-5-基；或者是2,3-二氢苯并[b][1,4]二噁烷-6-基；R2是氢、较低烷基或被烷氧基取代的较低烷基；R3是氢、较低烷基、被卤素取代的较低烷基、被羟基取代的较低烷基、NH-S(O)2-CH3、-(CH2)m-O-较低烷基或-(CH2)n-S(O)2-CH3；或者是-(CR2)n-苯基，可选择地被-S(O)2CH3或较低烷氧基取代；或者是-(CH2)n-杂环烷基，可选择地被较低烷基和=O取代；或者是-(CH2)n-杂芳基，可选择地被一个或两个较低烷基基团取代；或者是-(CH2)n-环烷基，可选择地被氰基取代；或者R2和R3与它们连接的N原子一起形成一个杂环环，所述杂环环选自吗啉、哌啶、1,1-二氧代-硫代吗啉或哌嗪，可被较低烷基或C(O)O-较低烷基取代，或者可形成一个吡咯烷环，可选择地被羟基取代；R独立于n是氢或较低烷基；n为0、1、2、3；m为2；或者是药学上可接受的酸盐，或者是外消旋混合物，或者是其对应的对映体和/或光学异构体，用于治疗精神分裂症、强迫性人格障碍、抑郁症、躁郁症、焦虑症、正常衰老、癫痫、视网膜退化、创伤性脑损伤、脊髓损伤、创伤后应激障碍、恐慌障碍、帕金森病、痴呆症、阿尔茨海默病、轻度认知障碍、化疗诱导的认知功能障碍（“化疗脑”）、唐氏综合征、自闭症谱系障碍、听力丧失、耳鸣、脊髓小脑共济失调、肌萎缩侧索硬化、多发性硬化症、亨廷顿病、中风，以及由放射治疗、慢性应激、视神经病变或黄斑变性引起的干扰，或者由酒精、阿片类药物、甲基苯丙胺、芬太尼或可卡因等神经活性药物的滥用引起的干扰。

  公开号：

  WO2014079787A1
• 作为产物：
  描述：

  4-甲砜基苯乙酮 在 氨 、 氢气 、 盐酸 作用下， 以 叔丁醇 为溶剂， 反应 24.0h， 生成 1-(4-(methylsulfonyl)phenyl)ethanamine hydrochloride
  参考文献：
  名称：

  可重复使用的镍纳米粒子催化的还原胺用于伯胺的选择性合成

  摘要：

  本文介绍了通过在二氧化硅上热解原位生成的酒石酸络合物来制备作为高效还原胺化催化剂的镍纳米粒子的方法。所得的稳定且可重复使用的镍纳米催化剂能够在分子氢存在下，从廉价且易于获得的羰基化合物和氨开始，合成功能化且结构多样的伯苄基，杂环和脂肪族胺。应用这种基于镍的胺化方案，可以将-NH 2部分引入结构复杂的化合物中，例如，类固醇衍生物和药物。

  DOI：

  10.1002/anie.201812100

文献信息

• Reusable Nickel Nanoparticles‐Catalyzed Reductive Amination for Selective Synthesis of Primary Amines
  作者：Kathiravan Murugesan、Matthias Beller、Rajenahally V. Jagadeesh

  DOI：10.1002/anie.201812100

  日期：2019.4

  The preparation of nickel nanoparticles as efficient reductive amination catalysts by pyrolysis of in situ generated Ni‐tartaric acid complex on silica is presented. The resulting stable and reusable Ni‐nanocatalyst enables the synthesis of functionalized and structurally diverse primary benzylic, heterocyclic and aliphatic amines starting from inexpensive and readily available carbonyl compounds and

  本文介绍了通过在二氧化硅上热解原位生成的酒石酸络合物来制备作为高效还原胺化催化剂的镍纳米粒子的方法。所得的稳定且可重复使用的镍纳米催化剂能够在分子氢存在下，从廉价且易于获得的羰基化合物和氨开始，合成功能化且结构多样的伯苄基，杂环和脂肪族胺。应用这种基于镍的胺化方案，可以将-NH 2部分引入结构复杂的化合物中，例如，类固醇衍生物和药物。
• SUBSTITUTED 1,6-NAPHTHYRIDINES
  申请人：Hoffmann-La Roche Inc.

  公开号：US20150252044A1

  公开（公告）日：2015-09-10

  The present invention relates to the use of compounds of general formula wherein R′ is hydrogen or lower alkyl; R 1 is halogen, lower alkyl, cycloalkyl or cyano; or is phenyl, optionally substituted by one to three substituents, selected from lower alkyl, lower alkyl substituted by halogen, lower alkoxy, lower alkoxy substituted by halogen, halogen, cyano, hydroxy, C(O)—NH-lower alkyl, CH 2 —C(O)—NH-lower alkyl, CH 2 —NH—C(O)-lower alkyl, CH 2 NH 2 , S(O) 2 CH 3 , S(O) 2 N(CH 3 ) 2 , or by heterocycloalkyl groups; or is pyrazol-1, 4 or 5-yl, optionally substituted by lower alkyl; or is thiazol-5-yl, optionally substituted by one or two lower alkyl groups; or is pyridine 2, 3 or 4-yl, optionally substituted by lower alkyl, lower alkoxy, halogen or N(CH 3 ) 2 ; or is 3,6-dihydro-2H-pyran; or is benzo[d][1,3]dioxol-5-yl; or is 2,3-dihydrobenzo[b][1,4]dioxin-6-yl; R 2 is hydrogen, lower alkyl or lower alkyl substituted by alkoxy; R 3 is hydrogen, lower alkyl, lower alkyl substituted by halogen, lower alkyl substituted by hydroxy, NH—S(O) 2 —CH 3 , —(CH 2 ) m —O-lower alkyl or —(CH 2 ) n —S(O) 2 —CH 3 ; or is —(CR 2 ) n -phenyl, optionally substituted by —S(O) 2 CH 3 or lower alkoxy; or is —(CH 2 ) n -heterocycloalkyl, optionally substituted by lower alkyl and ═O; or is —(CH 2 ) n -heteroaryl, optionally substituted by one or two lower alkyl groups; or is —(CH 2 ) n -cycloalkyl, optionally substituted by cyano; or R 2 and R 3 form together with the N atom to which they are attached a heterocyclic ring, selected from morpholine, piperidine, 1,1-dioxo-thiomorpholine or piperazine which may be substituted by lower alkyl or C(O)O-lower alkyl, or may form a pyrrolidine ring, optionally substituted by hydroxy; R is independently from n hydrogen or lower alkyl; n is 0, 1, 2, 3; m is 2; or to a pharmaceutically acceptable acid addition salt, to a racemic mixture or to its corresponding enantiomer and/or optical isomers thereof, for the treatment of schizophrenia, obsessive-compulsive personality disorder, depression, bipolar disorders, anxiety disorders, normal aging, epilepsy, retinal degeneration, traumatic brain injury, spinal cord injury, post-traumatic stress disorder, panic disorder, Parkinson's disease, dementia, Alzheimer's disease, mild cognitive impairment, chemotherapy-induced cognitive dysfunction (“chemobrain”), Down syndrome, autism spectrum disorders, hearing loss, tinnitus, spinocerebellar ataxia, amyotrophic lateral sclerosis, multiple sclerosis, Huntington's disease, stroke, and disturbances due to radiation therapy, chronic stress, optic neuropathy or macular degeneration, or abuse of neuro-active drugs selected from alcohol, opiates, methamphetamine, phencyclidine or cocaine.

  本发明涉及通式化合物的使用，其中R′为氢或低碳基；R1为卤素，低碳基，环烷基或氰基；或为苯基，可选地被一到三个取代基取代，所述取代基从低碳基，被卤素取代的低碳基，低碳氧基，被卤素取代的低碳氧基，卤素，氰基，羟基，C（O）-NH-低碳基，CH2-C（O）-NH-低碳基，CH2-NH-C（O）-低碳基，CH2NH2，S（O）2CH3，S（O）2N（CH3）2或杂环烷基组成；或为吡唑-1、4或5-基，可选地被低碳基取代；或为噻唑-5-基，可选地被一或两个低碳基取代；或为吡啶2、3或4-基，可选地被低碳基，低碳氧基，卤素或N（CH3）2取代；或为3,6-二氢-2H-吡喃基；或为苯并[d][1,3]二噁英-5-基；或为2,3-二氢苯并[b][1,4]二噁英-6-基；R2为氢，低碳基或被烷氧基取代的低碳基；R3为氢，低碳基，被卤素取代的低碳基，被羟基取代的低碳基，NH-S（O）2-CH3，（CH2）m-O-低碳基或（CH2）n-S（O）2-CH3；或为-（CR2）n-苯基，可选地被-S（O）2CH3或低碳氧基取代；或为-（CH2）n-杂环烷基，可选地被低碳基和═O取代；或为-（CH2）n-杂环芳基，可选地被一或两个低碳基取代；或为-（CH2）n-环烷基，可选地被氰基取代；或R2和R3与它们附着的N原子一起形成一个杂环环，所述杂环环从吗啉，哌啶，1,1-二氧-硫代吗啉或哌嗪中选择，所述杂环环可以被低碳基或C（O）O-低碳基取代，或可以形成一个吡咯烷环，可选地被羟基取代；R独立于n为氢或低碳基；n为0,1,2,3；m为2；或为其相应的对映异构体和/或光学异构体的药学上可接受的酸盐或外消旋体，用于治疗精神分裂症，强迫性人格障碍，抑郁症，双相情感障碍，焦虑症，正常衰老，癫痫，视网膜退化，创伤性脑损伤，脊髓损伤，创伤后应激障碍，恐慌症，帕金森病，痴呆，阿尔茨海默病，轻度认知障碍，化疗引起的认知功能障碍（“化疗脑”），唐氏综合症，自闭症谱系障碍，听力损失，耳鸣，脊髓小脑性共济失调，肌萎缩侧索硬化症，多发性硬化症，亨廷顿病，中风以及由放射治疗，慢性压力，视神经病变或黄斑变性，或滥用酒精，阿片类药物，甲基苯丙胺，苯环利定或可卡因等神经活性药物引起的干扰。
• US9657014B2
  申请人：——

  公开号：US9657014B2

  公开（公告）日：2017-05-23
• [EN] N-BIPHENYLMETHYLINDOLE MODULATORS OF PPARG<br/>[FR] MODULATEURS N-BIPHÉNYLMÉTHYLINDOLE DE PPARG
  申请人：KAMENECKA THEODORE MARK

  公开号：WO2012170554A1

  公开（公告）日：2012-12-13

  The invention provides molecular entities that bind with high affinity to PPARG (PPARƴ), inhibit kinase-mediated, e.g., cdk5-mediated, phosphorylation of PPARG, but do not exert an agonistic effect on PPARG. Compounds of the invention can be used for treatment of conditions in patients wherein PPARG plays a role, such as diabetes, insulin resistance, impaired glucose tolerance, prediabetes, hyperglycemia, hyperinsulinemia, obesity, or inflammation. In methods of treatment of these conditions using a compound of the invention, the compound can avoid producing side effects of significant weight gain, edema, impairment of bone growth or formation, or cardiac hypertrophy, or any combination thereof, in the patient receiving the compound. Methods of preparation of the compounds, bioassay methods for evaluating compounds of the invention as non-agonistic PPARG binding compounds, and pharmaceutical compositions are also provided.
• [EN] SUBSTITUTED 1,6-NAPHTHYRIDINES<br/>[FR] 1,6-NAPHTYRIDINES SUBSTITUÉES
  申请人：HOFFMANN LA ROCHE

  公开号：WO2014079787A1

  公开（公告）日：2014-05-30

  The present invention relates to the use of compounds of general formula (I) wherein R' is hydrogen or lower alkyl; R1 is halogen, lower alkyl, cycloalkyl or cyano; or is phenyl, optionally substituted by one to three substituents, selected from lower alkyl, lower alkyl substituted by halogen, lower alkoxy, lower alkoxy substituted by halogen, halogen, cyano, hydroxy, C(O)-NH-lower alkyl, CH2-C(O)-NH-lower alkyl, CH2-NH-C(O)-lower alkyl, CH2NH2, S(O)2CH3, S(O)2N(CH3)2, or by heterocycloalkyl groups; or is pyrazol-1, 4 or 5-yl, optionally substituted by lower alkyl; or is thiazol-5-yl, optionally substituted by one or two lower alkyl groups; or is pyridine 2, 3 or 4-yl, optionally substituted by lower alkyl, lower alkoxy, halogen or N(CH3)2; or is 3,6-dihydro-2H-pyran; or is benzo[d][1,3]dioxol-5-yl; or is 2,3-dihydrobenzo[b][1,4]dioxin-6-yl; R2 is hydrogen, lower alkyl or lower alkyl substituted by alkoxy; R3 is hydrogen, lower alkyl, lower alkyl substituted by halogen, lower alkyl substituted by hydroxy, NH-S(O)2-CH3, -(CH2)m-O-lower alkyl or -(CH2)n-S(O)2-CH3; or is -(CR2)n-phenyl, optionally substituted by -S(O)2CH3 or lower alkoxy; or is -(CH2)n-heterocycloalkyl, optionally substituted by lower alkyl and =O; or is -(CH2)n-heteroaryl, optionally substituted by one or two lower alkyl groups; or is -(CH2)n-cycloalkyl, optionally substituted by cyano; or R2 and R3 form together with the N atom to which they are attached a heterocyclic ring, selected from morpholine, piperidine, 1, 1-dioxo-thiomorpholine or piperazine which may be substituted by lower alkyl or C(O)O-lower alkyl, or may form a pyrrolidine ring, optionally substituted by hydroxy; R is independently from n hydrogen or lower alkyl; n is 0, 1, 2, 3; m is 2; or to a pharmaceutically acceptable acid addition salt, to a racemic mixture or to its corresponding enantiomer and/or optical isomers thereof, for the treatment of schizophrenia, obsessive-compulsive personality disorder, depression, bipolar disorders, anxiety disorders, normal aging, epilepsy, retinal degeneration, traumatic brain injury, spinal cord injury, post-traumatic stress disorder, panic disorder, Parkinson's disease, dementia, Alzheimer's disease, mild cognitive impairment, chemotherapy-induced cognitive dysfunction ("chemobrain"), Down syndrome, autism spectrum disorders, hearing loss, tinnitus, spinocerebellar ataxia, amyotrophic lateral sclerosis, multiple sclerosis, Huntington's disease, stroke, and disturbances due to radiation therapy, chronic stress, optic neuropathy or macular degeneration, or abuse of neuro-active drugs selected from alcohol, opiates, methamphetamine, phencyclidine or cocaine.

  本发明涉及使用一般式（I）的化合物，其中R'是氢或较低的烷基；R1是卤素、较低的烷基、环烷基或氰基；或者是苯基，可选择地被一个到三个取代基取代，所述取代基选自较低的烷基、被卤素取代的较低烷基、较低的烷氧基、被卤素取代的较低烷氧基、卤素、氰基、羟基、C(O)-NH-较低烷基、CH2-C(O)-NH-较低烷基、CH2-NH-C(O)-较低烷基、CH2NH2、S(O)2CH3、S(O)2N(CH3)2，或者是由杂环烷基组成的基团；或者是吡唑-1、4或5-基，可选择地被较低烷基取代；或者是噻唑-5-基，可选择地被一个或两个较低烷基基团取代；或者是吡啶-2、3或4-基，可选择地被较低烷基、较低烷氧基、卤素或N(CH3)2取代；或者是3,6-二氢-2H-吡喃；或者是苯并[d][1,3]二噁嗪-5-基；或者是2,3-二氢苯并[b][1,4]二噁烷-6-基；R2是氢、较低烷基或被烷氧基取代的较低烷基；R3是氢、较低烷基、被卤素取代的较低烷基、被羟基取代的较低烷基、NH-S(O)2-CH3、-(CH2)m-O-较低烷基或-(CH2)n-S(O)2-CH3；或者是-(CR2)n-苯基，可选择地被-S(O)2CH3或较低烷氧基取代；或者是-(CH2)n-杂环烷基，可选择地被较低烷基和=O取代；或者是-(CH2)n-杂芳基，可选择地被一个或两个较低烷基基团取代；或者是-(CH2)n-环烷基，可选择地被氰基取代；或者R2和R3与它们连接的N原子一起形成一个杂环环，所述杂环环选自吗啉、哌啶、1,1-二氧代-硫代吗啉或哌嗪，可被较低烷基或C(O)O-较低烷基取代，或者可形成一个吡咯烷环，可选择地被羟基取代；R独立于n是氢或较低烷基；n为0、1、2、3；m为2；或者是药学上可接受的酸盐，或者是外消旋混合物，或者是其对应的对映体和/或光学异构体，用于治疗精神分裂症、强迫性人格障碍、抑郁症、躁郁症、焦虑症、正常衰老、癫痫、视网膜退化、创伤性脑损伤、脊髓损伤、创伤后应激障碍、恐慌障碍、帕金森病、痴呆症、阿尔茨海默病、轻度认知障碍、化疗诱导的认知功能障碍（“化疗脑”）、唐氏综合征、自闭症谱系障碍、听力丧失、耳鸣、脊髓小脑共济失调、肌萎缩侧索硬化、多发性硬化症、亨廷顿病、中风，以及由放射治疗、慢性应激、视神经病变或黄斑变性引起的干扰，或者由酒精、阿片类药物、甲基苯丙胺、芬太尼或可卡因等神经活性药物的滥用引起的干扰。