ethyl 3-isopropyl-[1,2,4]thiadiazole-5-carboxylate | 180970-55-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 3-isopropyl-[1,2,4]thiadiazole-5-carboxylate
• 英文别名: ethyl 3-isopropyl-1,2,4-thiadiazole-5-carboxylate；ethyl 3-propan-2-yl-1,2,4-thiadiazole-5-carboxylate
• CAS: 180970-55-2
• 化学式: C₈H₁₂N₂O₂S
• 分子量: 200.261
• InChiKey: IPCWFCNYWRGHHC-UHFFFAOYSA-N

物化性质

• 沸点：
  291.1±23.0 °C(Predicted)
• 密度：
  1.179±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 3-isopropyl-[1,2,4]thiadiazole-5-carboxylate 、 N4-(3-溴苯基)喹唑啉-4,6-二胺 在 potassium tert-butylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.13h， 以50%的产率得到N-(4-(3-bromoanilino)quinazolin-6-yl)-3-isopropyl-1,2,4-thiadiazole-5-carboxamide
  参考文献：
  名称：

  Novel Irreversible Epidermal Growth Factor Receptor Inhibitors by Chemical Modulation of the Cysteine-Trap Portion

  摘要：

  Irreversible EGFR inhibitors can circumvent acquired resistance to first-generation reversible, ATP-competitive inhibitors in the treatment of non-small-cell lung cancer. They contain both a driver group, which assures target recognition, and it warhead, generally an acrylamide or propargylamide fragment that binds covalently to Cys797 within the kinase domain of EGFR. We performed it systematic exploration of the role for the warhead group, introducing different cysteine-trapping fragments at position 6 of a traditional 4-anilinoquinazoline scaffold. We found that different reactive groups, including epoxyamides (compounds 3-6) and phenoxyacetamides (compounds 7-9), were able to irreversibly inhibit EGFR. In particular, at significant lower concentrations than gefitinib (1), (2R,3R)-N-(4-(3-bromoanilino)quinazolin-6-yl)-3-(piperidin-1-ylmethyl)oxirane-2-carboxamide (6) inhibited EGFR autophosphorylation and downstream Signaling pathways, Suppressed proliferation, and induced apoptosis in gefitinib-resistant NSCLC H 1975 cells, harboring the T790M mutation in EGFR.

  DOI：

  10.1021/jm901558p
• 作为产物：
  描述：

  5-isopropyl-[1,3,4]oxathiazolin-2-one 、 氰基甲酸乙酯 以 对二甲苯 为溶剂， 反应 6.0h， 以to give crude ethyl 3-isopropyl-[1,2,4]thiadiazole-5-carboxylate (25.2 g, 97%) as a yellow oil, which的产率得到ethyl 3-isopropyl-[1,2,4]thiadiazole-5-carboxylate
  参考文献：
  名称：

  Herbicidal [1,2,4] thiadiazoles

  摘要：

  通式为##STR1##的新型除草剂化合物，其中A代表可选取代的烷基，烯基，环烷基，环烯基，芳基，杂芳基，芳基烷基或杂芳基烷基基团；R.sup.1代表氢原子或酰基基团；R.sup.2代表可选取代的烷基，烯基，芳基，杂芳基，芳基烷基或杂芳基烷基基团。

  公开号：

  US05583092A1

文献信息

• Herbicidal (1,2,4)thiadiazoles
  申请人：AMERICAN CYANAMID COMPANY

  公开号：EP0726260A1

  公开（公告）日：1996-08-14

  Novel herbicidal compounds of the general formula wherein A represents an optionally substituted alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, heteroaryl, aralkyl or heteroaralkyl group; R1 represents a hydrogen atom or an acyl group; and R2 represents an optionally substituted alkyl, alkenyl, aryl, heteroaryl, aralkyl or heteroaralkyl group.

  通式如下的新型除草化合物 其中 A 代表任选取代的烷基、烯基、环烷基、环烯基、芳基、杂芳基、芳烷基或杂烷基；R1 代表氢原子或酰基；R2 代表任选取代的烷基、烯基、芳基、杂芳基、芳烷基或杂烷基。
• Herbidical 1,2,4 thiadiazoles
  申请人：American Cyanamid Company

  公开号：EP0726261A1

  公开（公告）日：1996-08-14

  Compounds of the general formula I or II wherein A represents an optionally substituted alkyl, alkenyl, cycloalkyl, cycloalkenyl, dialkylamino, aryl, heteroaryl, aralkyl or heteroaralkyl group; R1 represents a hydrogen atom or an acyl group; and R2 represents an optionally substituted alkyl, alkenyl, aryl, heteroaryl, aralkyl or heteroaralkyl group are useful as herbicides. They are new per se except for the N-benzylamide of 5-(2-furyl)-1,2,4-thiadiazole-3-carboxylic acid.

  通式 I 或 II 的化合物 其中 A 代表任选取代的烷基、烯基、环烷基、环烯基、二烷基氨基、芳基、杂芳基、芳烷基或杂烷基；R1 代表氢原子或酰基；R2 代表任选取代的烷基、烯基、芳基、杂芳基、芳烷基或杂烷基。除了 5-(2-呋喃基)-1,2,4-噻二唑-3-羧酸的 N-苄基酰胺外，它们本身就是新产品。
• Drug efflux pump inhibitor
  申请人：DAIICHI PHARMACEUTICAL CO., LTD.

  公开号：EP1652839A2

  公开（公告）日：2006-05-03

  A medicament for preventive and/or therapeutic treatment of a microbial infection having an activity of eliminating resistance of a microorganism with acquired resistance to an antimicrobial agent, which comprises as an active ingredient a compound represented by the following general formula (I), a physiologically acceptable salt thereof, or a hydrate thereof: wherein R1 and R2 independently represent hydrogen atom, a halogen atom, carboxyl group and the like; J1 represents a 5- or 6-membered heteroaromatic ring; W1 represents -CH=CH-, -C≡C-, -CH2CH2- and the like; A1 represents phenylene group, pyridinediyl group, furandiyl group and the like; G1 represents oxygen atom, carbonyl group, ethynyl group and the like; p represents an integer of from 0 to 3; G2 represents phenylene group, furandiyl group, tetrahydrofurandiyl group and the like; G3 represents -CH2- or single bond; m and n represent an integer of 0 or 1; and Q1 represents an acidic group.

  一种用于预防和/或治疗微生物感染的药物，具有消除对抗菌剂产生抗药性的微生物的抗药性的活性，其活性成分包括下式（I）所代表的化合物、其生理上可接受的盐或其水合物： 其中 R1 和 R2 分别代表氢原子、卤素原子、羧基等；J1 代表 5 或 6 元杂芳环；W1 代表 -CH=CH-、-C≡C-、-CH2CH2- 等；A1 代表亚苯基、吡啶二基、呋喃二基等；G1 代表氧原子、羰基、乙炔基等；p 代表 0 至 3 的整数；G2 代表亚苯基、呋喃二基、四氢呋喃二基等；G3 代表 -CH2- 或单键；m 和 n 代表 0 或 1 的整数；以及 Q1 代表酸性基团。
• DRUG DISCHARGE PUMP INHIBITORS
  申请人：Trine Pharmaceuticals, Inc.

  公开号：EP1227084B1

  公开（公告）日：2005-12-14
• US5583092A
  申请人：——

  公开号：US5583092A

  公开（公告）日：1996-12-10