N,N-diethyl-3-(4-nitrophenoxy)propan-1-amine | 23999-21-5

• 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: N,N-diethyl-3-(4-nitrophenoxy)propan-1-amine
• 英文别名: 4-(diethylaminopropanoxy)-1-nitrobenzene；diethyl-[3-(4-nitro-phenoxy)-propyl]-amine；Diaethyl-[3-(4-nitro-phenoxy)-propyl]-amin；N-[3-(4-nitrophenoxy)-propyl]-diethylamine；diethyl-[3-(4-nitrophenoxy)-propyl]-amine；p-Nitrophenyl-3-diethylamino-propylether
• CAS: 23999-21-5
• 化学式: C₁₃H₂₀N₂O₃
• 分子量: 252.313
• InChiKey: OFSUBZOEFLPRFA-UHFFFAOYSA-N

物化性质

• 沸点：
  144-146 °C(Press: 0.4 Torr)
• 密度：
  1.089±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  58.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N-diethyl-3-(4-nitrophenoxy)propan-1-amine 在 palladium 10% on activated carbon 、 氢气 、 sodium acetate 作用下， 以 甲醇 、 乙醇 、 水 、 溶剂黄146 为溶剂， 生成 3-[4-[3-(Diethylamino)propoxy]phenyl]-5-[3-[4-(dimethylamino)phenyl]prop-2-enylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
  参考文献：
  名称：

  Discovery of potent and selective rhodanine type IKKβ inhibitors by hit-to-lead strategy

  摘要：

  Regulation of NF-kappa B activation through the inhibition of IKK beta has been identified as a promising target for the treatment of inflammatory and autoimmune disease such as rheumatoid arthritis. In order to develop novel IKK beta inhibitors, we performed high throughput screening toward around 8000 library compounds, and identified a hit compound containing rhodanine moiety. We modified the structure of hit compound to obtain potent and selective IKK beta inhibitors. Throughout hit-to-lead studies, we have discovered optimized compounds which possess blocking effect toward NF-kappa B activation and TNF alpha production in cell as well as inhibition activity against IKK beta. Among them, compound 3q showed the potent inhibitory activity against IKK beta, and excellent selectivity over other kinases such as p38 alpha, p38 beta, JNK1, JNK2, and JNK3 as well as IKK alpha. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.06.088
• 作为产物：
  描述：

  对硝基苯酚 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 生成 N,N-diethyl-3-(4-nitrophenoxy)propan-1-amine
  参考文献：
  名称：

  Discovery of potent and selective rhodanine type IKKβ inhibitors by hit-to-lead strategy

  摘要：

  Regulation of NF-kappa B activation through the inhibition of IKK beta has been identified as a promising target for the treatment of inflammatory and autoimmune disease such as rheumatoid arthritis. In order to develop novel IKK beta inhibitors, we performed high throughput screening toward around 8000 library compounds, and identified a hit compound containing rhodanine moiety. We modified the structure of hit compound to obtain potent and selective IKK beta inhibitors. Throughout hit-to-lead studies, we have discovered optimized compounds which possess blocking effect toward NF-kappa B activation and TNF alpha production in cell as well as inhibition activity against IKK beta. Among them, compound 3q showed the potent inhibitory activity against IKK beta, and excellent selectivity over other kinases such as p38 alpha, p38 beta, JNK1, JNK2, and JNK3 as well as IKK alpha. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.06.088

文献信息

• SUBSTITUTED NAPHTHYRIDINES AND USE THEREOF AS MEDICINES
  申请人：Hoffmann Matthias

  公开号：US20110201608A1

  公开（公告）日：2011-08-18

  The invention relates to new substituted naphthyridines of formula 1, as well as pharmacologically acceptable salts, diastereomers, enantiomers, racemates, hydrates or solvates thereof, wherein R 1 denotes a group A selected from among —O—R 3 , —NR 3 R 4 , —CR 3 R 4 R 5 , -(ethyne)-R 3 , —S—R 3 , —SO—R 3 and SO 2 —R 3 or R 1 denotes a group B selected from among C 6-10 -aryl, five- to ten-membered, mono- or bicyclic heteroaryl with 1-3 heteroatoms selected independently of one another from among N, O and S; while this heteroaryl is linked to the structure according to formula 1 via either a C atom or an N atom, three- to ten-membered, mono- or bicyclic, saturated or partially saturated heterocyclic group with 1-3 heteroatoms selected independently of one another from among N, O and S, while this heterocyclic group is linked to the structure according to formula 1 via either a C atom or an N atom, and 5- to 11-membered spiro group which may optionally contain 1, 2 or 3 heteroatoms selected independently of one another from among N, O and S, while this spiro group is linked to the structure according to formula 1 via either a C atom or an N atom, while this group B may optionally be substituted as described in claim 1 and wherein R 2 is and R 3 , R 4 , R 5 , R 6 , R 6′ , R 7 , R 8 , R 9 , R 10 , V, n and m may have the meanings given in claim 1 , as well as pharmaceutical compositions containing these compounds.

  该发明涉及公式1的新取代萘啉类化合物，以及其药理学上可接受的盐、对映体、对映异构体、外消旋体、水合物或溶剂合物，其中R1表示从以下选取的A基团，包括—O—R3、—NR3R4、—CR3R4R5、-(乙炔)-R3、—S—R3、—SO—R3和SO2—R3，或R1表示从以下选取的B基团，包括C6-10-芳基、含有1-3个异原子（N、O和S）的五至十元杂环芳基，而此杂环芳基通过碳原子或氮原子与公式1中的结构连接，含有1-3个异原子（N、O和S）的三至十元杂环饱和或部分饱和环族基团，而此杂环基团通过碳原子或氮原子与公式1中的结构连接，以及可能含有1、2或3个异原子（N、O和S）的五至十一元螺环基团，而此螺环基团通过碳原子或氮原子与公式1中的结构连接，其中该B基团可以选择地按照权利要求1中所述进行取代，R2为，R3、R4、R5、R6、R6′、R7、R8、R9、R10、V、n和m的含义如权利要求1中所述，以及含有这些化合物的药物组合物。
• SAR optimization studies on a novel series of 2-anilinopyrimidines as selective inhibitors against triple-negative breast cancer cell line MDA-MB-468
  作者：Jeyun Jo、Heegyu Kim、Ji Youn Oh、Soyeong Kim、Yeong Hye Park、Hyeonjin Choi、Jee-Yeong Jeong、Young-Suk Jung、Hwayoung Yun

  DOI：10.1016/j.bmcl.2019.126752

  日期：2019.12

  synthesized two series of 2-anilinopyrimidines based on the structure of our previously reported compound 1 that act as a selective inhibitor of the basal-like TNBC cell line MDA-MB-468. Through the fine-tuning of 1, cyclic and acyclic amines at 4-position of the pyrimidine core were turned out to be crucial for the selectivity. An extensive analysis of structure-activity relationships of the analogs revealed

  三阴性乳腺癌（TNBC）约占乳腺癌病例的15％，并且表现出侵略性的临床行为。在这项研究中，我们基于先前报道的化合物1的结构设计和合成了两个系列的2-苯胺基嘧啶，它们可作为基础样TNBC细胞系MDA-MB-468的选择性抑制剂。通过对1的精细调节，发现嘧啶核4位的环状和无环胺对于选择性至关重要。对类似物的结构-活性关系的广泛分析表明，丙基链末端的氨基烷基易于修饰。在新合成的类似物中，带有4-氯哌啶和环己基的化合物38被发现是最有效和最具选择性的，
• 신규한 2-아닐리노피리미딘 유도체 및 이를 포함하는 조성물
  申请人：Pusan National University Industry-University Cooperation Foundation 부산대학교 산학협력단(220040044843) BRN ▼621-82-06530

  公开号：KR20180085701A

  公开（公告）日：2018-07-27

  본 발명은 하기 화학식 1로 표시되는 2-아닐리노피리미딘 유도체 및 이를 유효성분으로 포함하는 암 예방 또는 치료용 조성물에 관한 것으로서, 상기 2-아닐리노피리미딘 유도체들은 신규한 물질로서 매우 뛰어난 표적 항암 효과를 나타내는 바, 상기 2-아닐리노피리미딘 유도체들을 포함하는 본 발명의 조성물들은 암 치료용 조성물 또는 예방 또는 개선용 조성물로서 유용하게 활용될 수 있다. [화학식 1] (상기 화학식 1에서, R은 4-(C1~C3)알킬피페라진(4-C(C1~C3)alkylpiperazine), 4-(C1~C3)알킬피페리딘(4-(C1~C3)alkylpiperidine), 피페리딘(piperidine), 피롤(pyrrole), 모르폴린(morpholine), 피롤리딘(pyrrolidine), 티오모르폴린(thiomorpholine), 인돌(indole), 다이(C1~C3)알킬아민(di(C1~C3)alkylamine) 및 4-할로피페리딘(4-halopiperidine)으로 이루어진 군에서 선택되는 어느 하나이고, R는 모르폴린(morpholine), 티오모르폴린(thiomorpholine), 피페리딘(piperidine), 다이(C1~C3)알킬아민(di(C1~C3)alkylamine), 사이클로(C3~C6)알킬(cyclo(C3~C6)alkyl) 및 (C1~C4)알콕시((C1~C4)alkoxy)로 이루어진 군에서 선택되는 어느 하나이다.)

  本发明涉及一种化学式1所示的2-芳基嘧啶衍生物及包含其作为有效成分的用于癌症预防或治疗的组合物，所述的2-芳基嘧啶衍生物作为一种新颖物质表现出非常优异的靶向抗癌效果，包含这些2-芳基嘧啶衍生物的本发明组合物可用作癌症治疗组合物或预防或改善组合物，具有很好的应用前景。【化学式1】（在上述化学式1中，R代表选择自4-(C1~C3)烷基哌嗪(4-C(C1~C3)alkylpiperazine)、4-(C1~C3)烷基哌啶(4-(C1~C3)alkylpiperidine)、哌啶(piperidine)、吡咯(pyrrole)、吗啉(morpholine)、吡咯啉(pyrrolidine)、硫代吗啉(thiomorpholine)、吲哚(indole)、二(C1~C3)烷基胺(di(C1~C3)alkylamine)和4-卤代哌啶(4-halopiperidine)中的一种，R代表选择自吗啉(morpholine)、硫代吗啉(thiomorpholine)、哌啶(piperidine)、二(C1~C3)烷基胺(di(C1~C3)alkylamine)、环(C3~C6)烷基(cyclo(C3~C6)alkyl)和(C1~C4)烷氧基((C1~C4)alkoxy)中的一种。）
• Non-imidazole aryloxy (or arylthio) alkylamines as histamine H3-receptor antagonists and their therapeutic applications
  申请人：SOCIETE CIVILE BIOPROJET

  公开号：EP0978512A1

  公开（公告）日：2000-02-09

  Compounds of formula (I): and their use for preparing medicaments acting as antagonists at the H3-receptors of histamine.

  式(I)的化合物及其用于制备作为组胺H3受体拮抗剂的药物。
• Non-imidazole alkylamines as histamine H3-receptor ligands and their therapeutic applications
  申请人：——

  公开号：US20040220225A1

  公开（公告）日：2004-11-04

  Use of a compound of formula (A), wherein: 1 W is a residue which imparts antagonistic and/or agonistic activity at histamine H 3 -receptors when attached to an imidazole ring in 4(5) position; R 1 and R 2 may be identical or different and represent each independently a lower alkyl or cycloalkyl, or taken together with the nitrogen atom to which they are attached, a saturated nitrogen-containing ring (i) as defined, a non-aromatic unsaturated nitrogen-containing ring (ii) as defined, a morpholino group, or a N-substituted piperazino group as defined for preparing medicaments acting as antagonists and/or agonists at the H 3 -receptors of histamine.

  使用式(A)的化合物，其中：1W是一个残基，当附加在咪唑环的4(5)位时，赋予组合物在组胺H3受体上的拮抗和/或激动活性；R1和R2可以相同也可以不同，分别独立地表示较低的烷基或环烷基，或者与它们所连接的氮原子一起，表示饱和的含氮环(i)、非芳香性不饱和含氮环(ii)、吗啡环或N-取代哌嗪环，用于制备在组胺H3受体上作为拮抗剂和/或激动剂的药物。